Tetrahydrofuran → HCID 15592215, compound

Participants

Reaction Steps

While under an argon atmosphere, a solution of the product of Example 3 (4 mmole) in tetrahydrofuran (100 ml) was cooled with stirring to ca.-75° C. n-Butyllithium (2 ml; 2.04 M in hexane) was added dropwise using a syringe over 15 min. After stirring for 2 hours a second solution of octadecyl aldehyde (4 mmole) in tetrahydrofuran (100 ml) precooled to -5° C. was canulated to the above solution over 25 min., maintaining the temperature below -60° C. The reaction was allowed to warm to room temperature over the next 2.5 hours, then was quenched with water (10 ml) and stirred for 60 hours. Most of the tetrahydrafuran was evaporated under a stream of nitrogen. More water (100 ml) was added and the mixture was extracted into ethyl acetate. The combined extracts were dried over sodium sulfate and filtered, then the solvent was removed by a nitrogen stream to give an oil. The product was purified by chromatography on silica gel to give 0.80 g of the title compound, m.p. ca.72°-75° C.

Provenance & Evidence