Methanesulfonyl chloride → HCID 90285103, compound

Temperature

5 °C

(R)-6-Methyl-hept-5-en-2-ol (1) (2.26 g, 17.6 mmol) and DIEA (5.52 mL, 31.7 mmol) were dissolved in anhydrous DCM (24 mL), the reaction mixture was cooled to 5° C., mesyl chloride (1.64 mL, 21.1 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 (60 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 (3.225 g, 86%). H1 NMR: see supporting information. TLC, Hexane-DCM-EtOAc, 40:40:20, 2 Rf 0.70 (developed with KMnO4 stain). 1H NNMR in CDCl3 (500 MHz): 5.08 ppm 1 Hm, 4.80 ppm 1 Hm, 2.99 ppm 3 Hs, 2.08 ppm 2 Hm, 1.75 ppm 1 Hm, 1.69 ppm 3 Hs, 1.624 1 Hm, 1.61 3 Hs, 1.43 ppm 3 Hd.

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-b4919164fde14c338bbebb070c9055e5

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403755B2