Carbon Dioxide → HCID 14478664, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2R 2-ethyl-2,3-epoxypropanol (2.6 g, 25.5 mmol) and copper iodide (475 mg, 2.5 mmol) was stirred in tetrahydrofuran (50 mL) under nitrogen and brought to -30° C. (dry ice, acetonitrile). Vinyl magnesium bromide [32 mL, 2M in tetrahydrofuran (THF), 2.5 eq] was added from a dropping funnel at such a rate as to maintain the temperature at -25° to -30° C. The reaction mixture was stirred at -30° C. for 2 h then brought to 0° C. and acidified with 10% HCl. The THF layer was separated and the aqueous phase was extracted with ether (3×50 mL). The organic layers were combined, dried over sodium sulfate, concentrated and distilled to give the title compound as a clear colorless oil (2.2 g, 60%, b.p. 85° C/5 mm). TLC Rf 0.26 (silica gel, 5% meOH in CH2Cl2, CAS/char:brown).

Provenance & Evidence