Triethylamine → Naphthalen-1-yl-carbamic acid 4-hydroxy-4-phenyl-butyl ester

Participants

Reaction Steps

1-Naphthyl isocyanate (4.3 ml, 30 mmol) in 50 ml of methylene chloride was added under nitrogen dropwise over 1 hour to a solution of 4-phenyl-4-hydroxybutanol (5.00 g, 30 mmol), prepared in step (a) of Example 6, and triethylamine (4.2 ml, 30 mmol) in 200 ml of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 18 hours. The solid present in the reaction was removed by filtration. The filtrate was extracted with 1 N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 10.08 g of a clear oil Purification of the oil by chromatography on 1 kg of silica gel (230-400 mesh) using 3%-20% ethyl acetate-methylene chloride as the eluent gave naphthalen-1-yl-carbamic acid 4-hydroxy-4-phenyl-butyl ester (7.73 g, 77%) as a white solid, mp 92-92° C.

Provenance & Evidence