(2S)-2-Methyloxirane → HCID 86685799, compound

Participants

Reaction Steps

Magnesium turnings (1.3 g, 55.2 mmol) were suspended in dry THF (50 mL) and to the mixture was added a pinch of iodine (20 mg) at room temperature. To this reaction mass was added a solution of 5-bromo-3-methylpent-1-ene (6 g, 36.8 mmol) in THF (200 mL). The reaction mass was heated with hot air gun to initiate the reaction. When the reaction was judged complete, the solution was cannulated to a solution of (S)-propylene oxide (3.21 g, 55.2 mmol) and copper bromide (0.528 g, 3.68 mmol) in THF (50 mL) at −78° C. The reaction mass was allowed to come to room temperature and stirred overnight. The reaction mass was quenched with saturated ammonium chloride solution and extracted with diethyl ether (200 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated at room temperature to get crude compound. The crude compound was purified by column chromotography (Silica gel, 10% TBME in pet ether) to get (2R)-6-methyloct-7-en-2-ol (12.4 g, 92%) as oily liquid. 1H NMR (400 MHz, CDCl3): δ ppm 5.82-5.69 (m, 1H), 4.98-4.91 (m, 2H), 4.27-4.26 (m, 1H), 3.65-3.39 (m, 1H), 2.15-1.98 (m, 1H), 1.36-1.19 (m, 5H), 1.18-1.1 (m, 1H), 1.08-0.95 (m, 5H), 0.89-0.78 (m, 1H).

Provenance & Evidence