Hydrochloric Acid → HCID 18728272, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(methyloxy)benzaldehyde (4.77 g, 35 mmol) in diethyl ether (100 mL) at 0° C. was added bromo(2-methylpropyl)magnesium (21 mL, 42 mmol). The solution was stirred for 10 min at 0° C. and then worked-up with 0.6M HCl (150 mL) and ethyl acetate (200 mL), to afford a crude material. In another round bottom flask of oxalyl chloride (4.60 mL, 52.5 mmol) in DCM (150 mL) at −78° C. was added DMSO (4.97 mL, 70.0 mmol), dissolved in dry DCM (20 mL), followed by a solution of the above crude material dissolved in dry DCM (25 mL). The resulting mixture was stirred for 1 h at −78° C., then triethylamine (24.39 mL, 175 mmol) was added and the solution stirred at −78° C. for 1 h. The reaction was quenched at −78° C. and the product was extracted by DCM and washed with water/brine. The crude material was purified by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in hexane, to afford the title compound (4.12 g). LCMS (B) m/z: 193 [M+1]+, Rt 3.11 min.

Provenance & Evidence