Lithium Hydroxide → HCID 90025778, compound

Participants

Reaction Steps

1-Amino-5-chloro-3,6-dimethylpyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate (100 mg, 269 μmol, Eq: 1.00) was added to a solution of ethyl 2-formylcyclopropanecarboxylate (38.2 mg, 269 μmol, Eq: 1.00) in methanol (2 ml). 2 N KOH aq (200 μl, 400 μmol, Eq: 1.49) was added and the yellow mixture was stirred for 1 h at room temperature under air. 1 N LiOH aq (4 mL, 4 mmol, Eq: 14.9) and tetrahydrofuran (8 ml) were added and the mixture was stirred for 30 min at room temperature. Volatile organic solvents were evaporated, water (10 ml) was added and the mixture was washed with diethyl ether (10 ml). The aqueous phase was acidified with 2 N HCl aq and then extracted with ethyl acetate (3×10 ml). The combined organic layers were dried over sodium sulfate and then concentrated to give the desired product (70 mg, 98%) as a white solid. MS: m/z=266.1 (M+H+)

Provenance & Evidence