Hydrochloric Acid → HCID 86675870, compound

Participants

Reaction Steps

A stirred solution of (R)-3-hydroxy-hept-6-enoic acid (J.C.S. Chem. Commun. 1983, 599-600, 0.4 g, 2.77 mmol) in anhydrous dichloromethane (20 mL) was treated with trimethyloxonium tetrafluoroborate (1.64 g, 11.08 mmol) and 1,8-bis(dimethylamino)naphthalene (3.56 g, 16.62 mmol). The reaction was stirred at room temperature under a nitrogen atmosphere for 16 hours then treated with 2 M hydrochloric acid (30 mL) and ethyl acetate (50 mL). The mixture was filtered to remove an insoluble solid before separating the two layers. The aqueous layer was extracted with further ethyl acetate (30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated to give a yellow gum which was purified by silica gel chromatography using iso-hexanes/ethyl acetate 17:3 to give the title compound (225 mg, 47%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ1.51-1.75 (m, 2H), 2.07-2.25 (m, 2H), 2.38-2.62 (m, 2H), 3.36 (s, 3H), 3.58-3.75 (m, 1H), 3.71 (s, 3H) 4.91-5.10 (m, 2H), 5.73-5.90 (m, 1H).

Provenance & Evidence