Potassium sodium tartarate → HCID 59656673, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-cyano-4-ethoxy-2-fluorobenzoic acid (3.0 g, 14.34 mmol) in THF (16 mL) and ether (8 mL) at −78° C. was added diisobutylaluminum hydride (DIBAL-H) solution (1 M in THF, 43.0 mL, 43.0 mmol). The reaction was allowed to warm to 0° C. over 3 h, and then it was stored at −10° C. overnight. 1M Sodium potassium tartrate (100 mL, 100 mmol) and diatomaceous earth were added and stirred at room temperature for 4 h. The mixture was filtered through a diatomaceous earth pad, extracted with dichloromethane, rinsed with saturated sodium bicarbonate solution, and rinsed with brine. It was dried over sodium sulfate, concentrated and dried in vacuo to give 6-ethoxy-3-hydroxymethyl-2-fluorobenzonitrile (2.352 g, 12.05 mmol, 63.0%) which was used as is in the next reaction.

Provenance & Evidence