Methanesulfonyl chloride → HCID 90286347, compound

Temperature

5 °C

(S)-6-Methyl-hept-5-en-2-ol (2.64 g, 20.58 mmol) and DIEA (6.45 mL, 37.0 mmol) were dissolved in anhydrous DCM (28 mL), the reaction mixture was cooled to 5° C., mesyl chloride (1.91 mL, 24.7 mmol) was added dropwise, and the reaction mixture was allowed to slowly warm to RT. After 18 h at RT the reaction mixture was diluted with DCM (100 mL), washed with water (3×35 mL), brine (35 mL), dried with MgSO4, solvent was concentrated to give a dark oil which was purified by SiO2 flash chromatography using Hexane-EtOAc to give the title compound as an oil (3.213 g, 76%). TLC, Hexane-DCM-EtOAc, 40:40:20, 2 Rf 0.70 (developed with KMnO4 stain). H1 NMR (CDCl3): • 5.08 (m, 1H), 4.80 (m, 1H), 2.99 (s, 3H), 2.10 (m, 2H), 1.75 (m, 1H), 1.69 (s, 3H), 1.62 (m, 1H), 1.61 (s, 3H), 1.43 (d, 3H, J=6.5 Hz).

1. temperatureto slowly warm to RT
2. washwashed with water (3×35 mL), brine (35 mL)
3. dry with materialdried with MgSO4, solvent
4. concentrationwas concentrated
5. customto give a dark oil which
6. customwas purified by SiO2 flash chromatography

ORD record

ord-6105d5a6651145509d27cc6cc308d8c9

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403755B2