Sodium hydride → HCID 53907933, compound

Participants

Reaction Steps

A solution of dimethyl-2-oxotridecylphosphonate (984 mg, 3.21 mmol) in tetrahydrofuran (25 ml) was added dropwise to a suspension of sodium hydride (128 mg; a 60% suspension in mineral oil) in tetrahydrofuran (5 ml) at 0° under argon. After 1.5 hours at room temperature, the mixture was cooled to 0° and a solution of 5-trimethylsilyl-3-furaldehyde (450 mg, 2.68 mmol) in tetrahydrofuran (15 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with 5% ammonium chloride and washed with 5% sodium bicarbonate and water. Evaporation of the dried (magnesium sulfate) organic phase gave a residue, which was purified by a silica column using 5% ethyl acetate/hexane to give the titled ketone.

Provenance & Evidence