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1
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0000863940
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Padwa, A, Ed, Wiley: New York
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2
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Easton, C.J.1
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10
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28244477555
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Schaumann, E, Ed, Georg Thieme Verlag: Stuttgart
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(a) Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 11; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2001, 229.
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14
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0030837671
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16
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0037413531
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Hulubei, V.6
Blumenfeld, A.7
Natale, N.R.8
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17
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20144389487
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Kaszubska, W.7
Colins, C.A.8
Sham, H.L.9
Liu, G.10
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18
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0344887064
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Although the pKa of methanesulfonylacetone (6) has not been documented so far, we estimated it to be higher than that of ethyl acetoacetate (3) by analogy from the pKa of dimethyl sulfone (31.1 in DMSO) and EtOAc (29.5 in DMSO, a) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456
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Although the pKa of methanesulfonylacetone (6) has not been documented so far, we estimated it to be higher than that of ethyl acetoacetate (3) by analogy from the pKa of dimethyl sulfone (31.1 in DMSO) and EtOAc (29.5 in DMSO): (a) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
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19
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33751386814
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(b) Zhang, X.-M.; Bordwell, F. G.; Van Der Puy, M.; Fried, H. E. J. Org. Chem. 1993, 58, 3060.
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J. Org. Chem
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Zhang, X.-M.1
Bordwell, F.G.2
Van Der Puy, M.3
Fried, H.E.4
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20
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34548863317
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Structure of 21 was confirmed by X-ray crystallographic analysis (CCDC 647875).
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Structure of 21 was confirmed by X-ray crystallographic analysis (CCDC 647875).
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21
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34548812539
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For conventional synthesis of the isoxazolone via the reaction of hydroxylamine and 3-oxo ester, see reference 4a. For the access from nitrile oxides, see: (a) Scarpati, R.; Sorrentino, P. Gazz. Chim. Ital. 1959, 8, 1525.
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For conventional synthesis of the isoxazolone via the reaction of hydroxylamine and 3-oxo ester, see reference 4a. For the access from nitrile oxides, see: (a) Scarpati, R.; Sorrentino, P. Gazz. Chim. Ital. 1959, 8, 1525.
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23
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34548851684
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Typical Experimental Procedure for the Synthesis of Isoxazole 14 Using 4 Å MS: To a solution of 2-bromo-6-methoxybenzonitrile oxide (12; 214 mg, 0.937 mmol) and benzoylacetonitrile (4; 161 mg, 1.11 mmol) in i-PrOH (3.1 mL) was added 4 Å MS (938 mg) at r.t. The red suspension was heated at 50°C for 2 h. After cooling, the mixture was filtered through a Celite® pad, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc, 85:15) to give 14 (253 mg, 76, as a yellow solid. Recrystallization of 14 from acetone-hexane gave a colorless prism; mp 177.2-177.6°C. 1H NMR (300 MHz, CDCl3, δ, 3.85 (s, 3 H, 7.00 (dd, J, 2.0, 7.6 Hz, 1 H, 7.33 (dd, J, 2.0, 7.6 Hz, 1 H, 7.37 (dd, J, 7.6, 7.6 Hz, 1 H, 7.55-7.64 (m, 3 H, 8.12-8.19 (m, 2 H, 13C NMR 75 MHz, CDCl3, δ, 56.1, 90.0, 110.2, 11
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1H NMR...
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