Ammonium Chloride → (S)-(+)-6-Methyl-5-hepten-2-ol

Temperature

0 °C

3-Methylbut-2-enylmagnesium chloride, 0.50 M in THF (100 mL, 50 mmol) was cooled to 0° C., CuI (952 mg, 5.0 mmol), then (S)-2-methyl-oxirane (1.752 mL, 25.0 mmol) in anhydrous THF (12 mL) was slowly added to the stirred reaction mixture via syringe pump at a rate of 16 mL/h over 45 min to give a dark suspension which was stirred at 0° C. under an Argon atm for 1 h, then allowed to slowly warm to RT over several h. After stirring at RT for 18 h the reaction mixture was poured into sat aqueous NH4Cl (75 mL), the mixture was extracted with Et2O (3×100 mL), the organic extracts were combined, washed with water (100 mL), brine (100 mL), dried with MgSO4, and solvent was evaporated in vacuo (30 mm Hg) at 25° C. to give an oil which was purified by SiO2 flash chromatography to give the title compound as an oil in 2 fractions (2.2 g, 69%). H1 NMR (CDCl3): • 5.14 (m, 1H), 3.82 (m, 1H), 3.08 (m, 1H), 1.69 (s, 3H), 1.62 (s, 2H), 1.48 (m, 2H), 1.19 (d, 3H, J=6 Hz).

1. customto give a dark suspension which
2. temperatureto slowly warm to RT over several h
3. stirringAfter stirring at RT for 18 h the reaction mixture
4. additionwas poured
5. extractionthe mixture was extracted with Et2O (3×100 mL)
6. washwashed with water (100 mL), brine (100 mL)
7. dry with materialdried with MgSO4, and solvent
8. customwas evaporated in vacuo (30 mm Hg) at 25° C.
9. customto give an oil which
10. customwas purified by SiO2 flash chromatography

ORD record

ord-54883d89a04f4b28b94e19db2f32a819

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403755B2