Methanesulfonyl chloride → HCID 56834266, compound

Temperature

0 °C

N,N-Diisopropylethylamine (15.5 g, 0.12 mol) was added to a solution of methyl 2,2-dimethyl-3-hydroxypropionate (13.2 g, 0.1 mol) in dichloromethane (150 mL) and the solution was cooled to 0° C. Methane sulfonyl chloride (12.6 g, 0.11 mol) was then added dropwise and the mixture was stirred at 0° C. for 90 minutes. The reaction mixture was then diluted with 0.5M hydrochloric acid (100 mL) and the layers were separated. The aqueous was extracted with dichloromethane (2×50 mL) and the combined organic solution was dried over magnesium sulfate and concentrated in vacuo. Methanethiol sodium salt (7.7 g, 0.11 mol) was added to a solution of the residue in dioxan (100 mL) and the mixture was heated under reflux for 24 hours. The mixture was then diluted with ethyl acetate (250 mL), washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography on silica gel, eluting with dichloromethane:pentane 50:50 to 100:0, afforded the title compound as a pale yellow oil in 24% yield, 3.85 g.

1. customthe layers were separated
2. extractionThe aqueous was extracted with dichloromethane (2×50 mL)
3. dry with materialthe combined organic solution was dried over magnesium sulfate
4. concentrationconcentrated in vacuo
5. temperaturethe mixture was heated
6. temperatureunder reflux for 24 hours
7. washwashed with water and brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customPurification by column chromatography on silica gel
11. washeluting with dichloromethane:pentane 50:50 to 100:0

ORD record

ord-e48bdc7f879d4b30a67dbdc9728ddab9

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076356B2