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1
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27744507729
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note
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A preliminary version of this work was presented at the 2003 National Organic Symposium, Bloomington, IN.
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4
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0028848907
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and references therein
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For a review, see: Benneche, T. Synthesis 1995, 1 and references therein.
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(1995)
Synthesis
, pp. 1
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Benneche, T.1
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5
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0000828038
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John Wiley & Sons: New York, Collect
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For a representative lab-scale procedure, see: Marvel, C. S.; Porter, P. K. Organic Syntheses; John Wiley & Sons: New York, 1941; Collect. Vol. I, p 377.
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(1941)
Organic Syntheses
, vol.1
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Marvel, C.S.1
Porter, P.K.2
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6
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27744531526
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U.S. Patent 3,972,947
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The majority of these processes rely on halide exchange between an acid chloride and dimethoxymethane, and typically employ elevated temperature and/or protic acid catalysis to accelerate the reaction. With HCl: (a) Weinstock, L. M.; Karady, S.; Sletzinger, M. U.S. Patent 3,972,947; Chem. Abstr. 1976, 85, 142633.
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Chem. Abstr.
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Weinstock, L.M.1
Karady, S.2
Sletzinger, M.3
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7
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84987497573
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(b) Amato, J. S.; Karady, S.; Sletzinger, M.; Weinstock, L. M. Synthesis 1979, 970.
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Amato, J.S.1
Karady, S.2
Sletzinger, M.3
Weinstock, L.M.4
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8
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0012765057
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(c) Linderman, R. J.; Jaber, M.; Griedel, B. D. J. Org. Chem. 1994, 59, 6499.
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Linderman, R.J.1
Jaber, M.2
Griedel, B.D.3
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10
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27744555617
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WO 02/059070 A1
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(e) Williams, A. G. WO 02/059070 A1; Chem. Abstr. 2002, 137, 124930.
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Chem. Abstr.
, vol.137
, pp. 124930
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Williams, A.G.1
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14
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27744525828
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John Wiley & Sons: New York
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For a summary of toxicological data and safety recommendations, see: (a) Sax's Dangerous Properties of Industrial Materials, 10th ed.; Lewis, R. J., Sr., Ed.; John Wiley & Sons: New York, 2000; Vol. 2, p 854.
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Sax's Dangerous Properties of Industrial Materials, 10th Ed.
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Lewis Sr., R.J.1
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15
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27744581033
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Sigma-Aldrich: Milwaukee, WI
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(b) Sigma-Aldrich Library of Chemical Safety Data, 2nd ed.; Lenga, R. E., Ed.; Sigma-Aldrich: Milwaukee, WI, 1988; Vol. 1, p 804.
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Sigma-Aldrich Library of Chemical Safety Data, 2nd Ed.
, vol.1
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Lenga, R.E.1
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16
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0024308309
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The carcinogenicity of MOMCl has been estimated to be greater than that of vinyl chloride; see Van Duuren, B. L. Environ. Res. 1989, 49, 143.
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(1989)
Environ. Res.
, vol.49
, pp. 143
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Van Duuren, B.L.1
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24
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0033515465
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Using other reagents: (h) Marcune, B. F.; Karady, S.; Dolling, U.-H.; Novak, T. J. J. Org. Chem. 1999, 64, 2446-2449.
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Marcune, B.F.1
Karady, S.2
Dolling, U.-H.3
Novak, T.J.4
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26
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0242408190
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Ledneczki, I.; Agócs, P. M.; Molnár, A. Synlett 2003, 14, 2255.
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Synlett
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Ledneczki, I.1
Agócs, P.M.2
Molnár, A.3
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28
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0026532855
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Chang, C.; Chu, K. C.; Yue, S. Synth. Commun. 1992, 22, 1217.
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(1992)
Synth. Commun.
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, pp. 1217
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Chang, C.1
Chu, K.C.2
Yue, S.3
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29
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85026888812
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Bailey, W. F.; Carson, M. W.; Zarcone, L. M. J. Org. Synth. 1998, 75, 177.
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, pp. 177
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Bailey, W.F.1
Carson, M.W.2
Zarcone, L.M.3
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30
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33751155514
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(b) Bailey, W. F.; Zarcone, L. M. J.; Rivera, A. D. J. Org. Chem. 1995, 60, 2532.
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Bailey, W.F.1
Zarcone, L.M.J.2
Rivera, A.D.3
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33
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27744587282
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note
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2 is employed, 2 mol % MOMBr is present in solution. Under typical reaction conditions with 0.01 mol % or less catalyst, α-halo ethers from the halogenation exchange process cannot be detected.
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35
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27744448949
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note
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1H NMR spectroscopy.
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-
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36
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27744608508
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note
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3 proceeds rapidly (less than 1 h) to 33% conversion, and then slows substantially, with 66% conversion after 16 h at 45 °C. In this instance, reaction endpoint monitoring is inaccurate because of the evaporative losses of the DMM and MOMCl during the extended reflux.
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37
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27744598670
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note
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The initial aqueous quench is mildly exothermic, and typically >98% of residual α-halo ether is decomposed when heat evolution has ceased, which is 5 min or less for preparative scale experiments (100 mmol scale). See Supporting Information for additional details.
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38
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0000919571
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Goff, D. A.; Harris, R. N., III; Bottaro, J. C.; Bedford, C. D. J. Org. Chem. 1986, 51, 4711.
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Goff, D.A.1
Harris III, R.N.2
Bottaro, J.C.3
Bedford, C.D.4
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