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

HRID 1460113Notes

Reaction equation

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]>>[Si:19]([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])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

Reactant 3

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamide

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

HCID 178418339Butyllithium

Product 1

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

Procedure

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-butyldimethylsilyloxy)-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).

Workup

customthe product was purified by chromatography on silica gel with hexane

Sources & evidence

ORD record: ord-61507e64eb924932b04f033ced474c2d
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854249

Reaction notes

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