Toluene → HCID 86758778, compound

Participants

Reaction Steps

To a suspension of methyltriphenylphosphonium bromide (5.2 g, 14.5 mmol) in anhydrous dioxane (75 mL) at room temperature under a nitrogen atmosphere, a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene (24.4 mL, 12.2 mmol) was added. After 1 hour, the mixture was added via cannula to a solution ethyl (1RS,5SR,6RS)-2-hydroxy-3-oxabicyclo[3.1.0]-hexane-6-carboxylate (1.0 g, 2.62 mmol) in anhydrous dioxane (25 mL) under a nitrogen atmosphere and the reaction mixture was stirred for 1 hour. Then, the mixture was poured onto a 2:1 mixture of diethyl ether and water (300 mL) and the layers were separated. The aqueous layer was extracted with diethyl ether (2×100 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography using ethyl acetate and hexane 1:2 as eluent to afford 840 mg (85% yield) of ethyl (1SR,2SR,3RS)-2-hydroxymethyl-3-vinylcyclopropane carboxylate.

Provenance & Evidence