Pyridine → 2,2,2-Trichloroethyl 10-hydroxydecanoate

Participants

Reaction Conditions

Reaction Steps

A solution of N,N′-dicyclohexylcarbodiimide (DCC, 2.41 g; 14.1 mmol) in dry dichloromethane (15 mL) was added drop-wise to a stirred solution of 10-hydroxydecanoic acid (1.88 g; 10.0 mmol), 2,2,2-trichloroethanol (6.13 g; 41.0 mmol), and pyridine (4.1 mL) in dry dichloromethane (35 mL) cooled to 0° C. (bath temperature) under argon. After stirring one hour at 0° C., the mixture was stirred at ambient temperature overnight. The reaction mixture was vacuum filtered and acetic acid (3 mL) was added to the filtrate. After standing 30 min, the mixture was refiltered and the filtrate was diluted with diethyl ether (150 mL). The solution was washed with 1 M HCl (3×25 mL), water (3×25 mL), saturated NaHCO3 solution (2×25 mL), and saturated NaCl solution (1×25 mL). After drying (MgSO4), filtration, and evaporation, the residue was purified by flash chromatography on a 170×25 mm silica gel 60 column eluted with ethyl acetate-hexane (1:1), collecting 12×25 mL fractions. Fractions 3-5 were evaporated and the residue was vacuum dried at 50° C. and 0.05 mm Hg on a Kugelrohr apparatus to remove excess 2,2,2-trichloroethanol. 2.1 g (66%) product was obtained (colorless oil).

Provenance & Evidence