Triethylamine → 2-Formyl-3-(tert-butyldimethylsilanyloxy)-5-methoxy-6-methylbenzoic acid allyl ester
Reaction equation
[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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customevaporated in vacuo
- washthe solution was washed successively with 1N hydrochloric acid, water and brine
- dry with materialThe organic layer was dried over sodium sulfate
- customThe solvent was evaporated in vacuo
- customthe solid residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-729178c747044f0bb42657ac8014b5bd
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05594135
Reaction notes
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