Sodium Bicarbonate → HCID 12691759, compound

Participants

Reaction Steps

A solution of 686 mg of 5-(methoxycarbonyl)-2,6-dimethylnicotinic acid and 8.0 mL of BH3.THF (1.0 M in THF) in 10 mL of THF was heated to 75° C. for 2.5 h. An aqueous solution of 3 mL of AcOH:H2O (1:1) was added, and the solution was stirred until the bubbling ceased. Saturated NaHCO3 was added to a pH=7, and the solution was stirred overnight. EtOAc and H2O were added, and the layers were separated. The aqueous layer was extracted with 30 mL of EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (3% MeOH/CHCl3) provided 452 mg of methyl 5-(hydroxymethyl)-2,6-dimethylnicotinate as a pale yellow solid in 71% yield.

Provenance & Evidence