Hydrochloric Acid → HCID 67119355, compound

Participants

Reaction Steps

A sec-butyl lithium-1.00M cyclohexane-n-hexane mixture solution (29.8 ml, 29.8 mmol) was added dropwise to a solution of 1-tert-butyl-3-(dimethoxymethyl)-2-(methoxymethoxy)benzene (4.00 g, 14.9 mmol) obtained in Example (10-1) and N,N,N′,N′-tetramethylethylenediamine (4.72 ml, 31.3 mmol) in diethyl ether (100 ml) at −40° C. over 20 minutes. After the reaction mixture was stirred at room temperature for 1 hour, it was cooled to −20° C. and N,N-dimethylformamide (2.30 ml, 31.3 mmol) was added thereto. After the temperature of the reaction mixture was returned to room temperature and the mixture was further stirred for 1 hour, the mixture was carefully poured into cold 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate (three times). The combined organic layer was successively washed with 0.1N hydrochloric acid, water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was dissolved in methanol (10 ml) and sodium borohydride (111 mg, 3.00 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (four times), the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-3/1) to give [4-tert-butyl-2-(dimethoxymethyl)-3-(methoxymethoxy)phenyl]methanol (350 mg, yield: 8%).

Provenance & Evidence