Tetrahydrofuran → HCID 19991618, compound

Participants

Reaction Steps

n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.58 ml, 1.44 mmol) was added dropwise to a solution of 1-tridecyne (259 mg, 1.44 mmol) in tetrahydrofuran (6 ml) at 0°. After 1 hour, a solution of (2-triethylsilyl-4-furyl)-1-propanal (312 mg, 1.31 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column using 15% ethyl ether/hexane to give the titled alcohol.

Provenance & Evidence