Triethylsilane → 1-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester (3.7 g) obtained in Step 1 and tris(triphenylphosphine) rhodium(I) chloride (163 mg) in toluene (80 mL) was added dropwise triethylsilane (5.9 mL) under argon atmosphere over 10 minutes, followed by stirring the reaction mixture at 55° C. for 27 hours. After cooling down to room temperature and adding aqueous sodium bicarbonate solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1) to give 1-triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester (5.0 g).

Provenance & Evidence