Chloride → Methyl 3,4-dimethoxy-5-(3-oxopropyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of oxallyl chloride (1.34 mL, 15.4 mmol) in CH2Cl2 (30 mL) at −78° C. was added a solution of dimethyl sulfoxide (DMSO) (1.45 mL, 20.5 mmol) in CH2Cl2 (10 mL) via cannula over the course of 1 min. After stirring for 20 min at −78° C. a solution of 3-(3-hydroxypropyl)-4,5-dimethoxybenzoic acid methyl ester (1.30 g, 5.12 mmol) in CH2Cl2 (10 mL) was added via syringe. The reaction was stirred at −78° C. for 45 min then treated with triethylamine (Et3N) (5.7 mL, 10 eq.). After 20 min at −78° C. the reaction was allowed to warm to room temperature. After stirring at room temperature for 30 min, the reaction mixture was diluted with 1:1 EtOAc:hexanes (250 mL), washed with H2O (2×200 mL), brine (200 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel using 50% EtOAc in hexanes as an eluent to furnish 3,4-dimethoxy-5-(3-oxopropyl)benzoic acid methyl ester (1.20 g, 93%).

Provenance & Evidence