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ref 7a
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(b) See ref 7a.
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24
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3743127860
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note
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The longer reaction and workup times involved in a large scale reaction were a concern for epimerization. On a 20 kg scale, a 42% yield was obtained for the combined reaction steps preparing 3 and 4. We believe the lower large scale yield was also due to larger than expected amounts of the corresponding alcohol present arising from overreduced aldehyde 3. Both of these factors contributed to the lower isolation yield in the crystallization process of 4. Pursuit in optimizing the scale-up process of this reaction was dropped due to finding a commercial kilogram quantity source for 5 (Nippon Kayaku Co., Ltd.).
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25
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0002626549
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For reviews, see: Shirley, D. A. Org. React. 1954, 8, 28. Jorgenson, M. J. Org. React. 1970, 18, 1.
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For reviews, see: Shirley, D. A. Org. React. 1954, 8, 28. Jorgenson, M. J. Org. React. 1970, 18, 1.
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This did not occur with LiCl. For related interest, see: Hendrix, J. C.; Halverson, K. J.; Jarrett, J. T.; Lanbury, P. T., Jr. J. Org. Chem. 1990, 55, 4517-4518. Claudy, P.; Bonnetot, B.; Mathurin, D.; Turck, G. Thermochim. Acta 1977, 20, 315-323.
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33
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3743085496
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This did not occur with LiCl. For related interest, see: Hendrix, J. C.; Halverson, K. J.; Jarrett, J. T.; Lanbury, P. T., Jr. J. Org. Chem. 1990, 55, 4517-4518. Claudy, P.; Bonnetot, B.; Mathurin, D.; Turck, G. Thermochim. Acta 1977, 20, 315-323.
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0002220787
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For related chemistry of carboxylate reactions with toluene and n-butyllithium, see: Lochmann, L.; Trekoval, J. J. Organomet. Chem. 1987, 326, 1-7. Schlosser, M.; Hartmann, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 508.
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84982344292
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For related chemistry of carboxylate reactions with toluene and n-butyllithium, see: Lochmann, L.; Trekoval, J. J. Organomet. Chem. 1987, 326, 1-7. Schlosser, M.; Hartmann, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 508.
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36
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3743148848
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note
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The aldehyde 3 could be stored for several days packed in dry ice without a change in optical purity measured by optical rotation.
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-
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37
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85086290548
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note
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