Tetrahydrofuran → HCID 15592210, compound

Participants

Reaction Steps

A solution of the product of Example 4 (4 mmoles) in tetrahydrofuran (150 ml) was cooled to ca. -75° C. under an atmosphere of argon. n-Butyllithium (2 ml, 2.04M in hexane) was added by syringe over 15 min. while maintaining the reaction temperature below -70° C., and the solution then stirred for 3.5 hours. A cold solution (ca. -8° C.) of octadecyl aldehyde (4 mmoles) in tetrahydrofuran (100 ml) was canulated by syringe to the above solution over 25 min., keeping the temperature below -60° C. The reaction temperature rose to 25° C. during the next 2 hours, after which the reaction was quenched with water (10 ml) and stirred overnight. After removing the tetrahydrofuran under a nitrogen stream, water (75 ml) was added and the product extracted into ethyl acetate. The combined extract was dried over sodium sulfate, filtered and stripped under reduced pressure to give 1.7 g of an oil. The product was purified by chromatography on silica gel to give 0.85 g of the title compound, m.p. ca. 74°-78° C.

Provenance & Evidence