6-Oxabicyclo[3.1.0]hexane → HCID 26595041, compound

Participants

Reaction Steps

To a solution of 3-methoxyphenyl magnesium bromide 1.0M (59.4 ml, 59.4 mmoles) and copper(I) iodide (0.762 g, 4.0 mmoles), add (dropwise) a solution of cyclopentene oxide (5.2 ml, 59.4 mmoles) in tetrahydrofuran (5 ml) over 40 minutes. The reaction is exothermic and the temperature rises to 45° C. Cool the reaction to ambient temperature and quench with a 25% solution of ammonium chloride (40 ml), extract with ether and shake with brine. Dry the organic layer over sodium sulfate and concentrate in vacuo to yield an oil which is flash chromatographed on silica with 14-25% ethyl acetate/hexanes to yield 6.43 g of the titled compound. 1H NMR (CDCl3): 7.23 (d, J=8.4, 1H), 6.86 (d, J=7.6 Hz, 1H), 6.81 (s, 1H), 6.77 (m, 1H), 4.15 (m, 1H), 3.81 (s, 3H), 2.86 (m, 1H), 2.18-2.04 (m, 2H), 1.9-1.6 (m, 5H).

Provenance & Evidence