Hydrochloric Acid → HCID 57864382, compound

Participants

Reaction Conditions

Reaction Steps

6.65 g (22 mmol) of 2-(4-tert-butylbenzyloxy)-5-fluorobenzoic acid are suspended in 25 ml of THF and cooled to 0° C. 2.4 ml (22 mmol) of N-methylmorpholine and 2.1 ml (22 mmol) of ethyl chloroformate are added, and the solution is stirred at room temperature for 15 min. 2.50 g (66 mmol) of sodium borohydride are added and, after 3 h, methanol is added until gas evolution has subsided. The mixture is acidified with 1 N hydrochloric acid and concentrated in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with saturated sodium chloride solution and then dried over sodium sulfate. The solvent is distilled out in vacuo, and the residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 3.52 g (12.2 mmol, 55% of theory) of the title compound are isolated.

Provenance & Evidence