4-Bromo-N,N-dimethylbenzenesulphonamide → 4-(3-(tert-butyldimethylsilyloxy)-alpha-hydroxybenzyl)-N,N-dimethylbenzenesulfonamide

HRID 2258346노트

반응식

HRID 2258346 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([Li])CCC.[Si:19]([O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=[O:31])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[C:22]([Si:19]([CH3:21])([CH3:20])[O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1)[OH:31])([CH3:25])([CH3:24])[CH3:23]

참가 물질

4

반응물 3

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 112071113-(t-Butyldimethylsilyloxy)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 545540284-(3-(tert-butyldimethylsilyloxy)-alpha-hydroxybenzyl)-N,N-dimethylbenzenesulfonamide수율 57%

실험 절차

The sulfonamide (97.45 g, 0.37 mol) was subsequently treated with n-butyllithium and 3-(tert-butyldimethylsilyloxy)benzaldehyde as described in Example 54, and the product was purified by chromatography on silica gel with hexane:ethyl acetate to give 89.5 g (57%) of 4-(3-(tert-butyldimethyl-silyloxy)-α-hydroxybenzyl)-N,N-dimethylbenzenesulfonamide as a yellow oil which crystallized on standing. A portion was recrystallized from ethanol:water to give white crystals, mp 100°-103° C. NMR (CDCl3, 60 MHz): δ0.1 (s, 6H); 0.9 (s, 9H); 2.6 (s, 6H); 3.5 (br s, 1H); 5.7 (s, 1H); 6.5-7.7 (m, 8H).

후처리

  1. customthe product was purified by chromatography on silica gel with hexane

출처 및 근거

ORD 기록
ord-ef03651ff1c94346a82e2e0f13a4c5fd
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05658908

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