Triethylamine → 2-Formyl-3-(tert-butyldimethylsilanyloxy)-5-methoxy-6-methylbenzoic acid allyl ester

HRID 234221

반응식

HRID 234221 반응식
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([OH:15])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3].[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[CH:9]=[C:8]([O:15][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25])[C:7]=1[CH:16]=[O:17])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 537352632-Formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester

생성물 1

HCID 538122792-Formyl-3-(tert-butyldimethylsilanyloxy)-5-methoxy-6-methylbenzoic acid allyl ester수율 93.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 15 g of 2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid allyl ester in 0.12 l of N,N-dimethylformamide were added 13.8 g of tert-butyl-dimethylchlorosilane and 12.0 g of triethylamine. The mixture was stirred for 3 h at room temperature and then evaporated in vacuo. The residue was taken up in 0.4 l of ethyl acetate and the solution was washed successively with 1N hydrochloric acid, water and brine. The organic layer was dried over sodium sulfate. The solvent was evaporated in vacuo and the solid residue was recrystallized from hexane to give 20.5 g of 2-formyl-3-(tert-butyldimethylsilanyloxy)-5-methoxy-6-methylbenzoic acid allyl ester as white crystals of m.p. 94°-95° C.

후처리

  1. customevaporated in vacuo
  2. washthe solution was washed successively with 1N hydrochloric acid, water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe solid residue was recrystallized from hexane

출처 및 근거

ORD 기록
ord-729178c747044f0bb42657ac8014b5bd
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594135

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