Acetonitrile → HCID 67496220, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 ml flask was added 30 ml of THF and acetonitrile (1.41 ml, 26.9 mmole). The mixture was cooled to −78° C. and then n-butyllithium (16.8 ml, 26.9 mmole, 1.6M solution in hexane) was added. The reaction was stirred for 30 minutes at which time 5 ml of a THF solution of methyl 2-methoxyisonicotinate 105.1.A (1.50 g, 9.0 mmole) was added. After 3 hours at −78° C., the reaction mixture was quenched by 1.7 ml of acetic acid, and was warmed to room temperature. The solvent was removed by rotary evaporation and the crude was purified on a silica gel column to give 105.1.B (676 mg, 43% yield) as orange crystals.

Provenance & Evidence