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

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).

1. temperatureThe reaction mass was heated with hot air gun
2. customthe reaction
3. customto come to room temperature
4. customThe reaction mass was quenched with saturated ammonium chloride solution
5. extractionextracted with diethyl ether (200 mL×3)
6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
7. concentrationconcentrated at room temperature
8. customto get crude compound
9. customThe crude compound was purified by column chromotography (Silica gel, 10% TBME in pet ether)

ORD record

ord-240d993aafc048faafb45c47b938a477

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691757B2