Triethylamine → 2-(1-Hydroxycyclopropyl)ethyl methanesulfonate

Temperature

-10 °C

A mixture of 1-(2-hydroxyethyl)cyclopropanol (86 mg, 0.843 mmol) and triethylamine (136 mg, 1.35 mmol, Shantou Xilong chemical factory) in 10 mL of dichloromethane was stirred at −10° C. for 30 min. Methanesulfonyl chloride (106 mg, 0.927 mmol, Shanghai Haiqu chemical Ltd.) was then added via a syringe. The reaction was stirred at −10° C. for 1 hr at rt and then quenched with 1 mL ice-water. The resulted mixture was extracted with dichloromethane (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to afford 2-(1-hydroxycyclopropyl)ethyl methanesulfonate as yellow oil (used in the next step without further purification).

1. stirringThe reaction was stirred at −10° C. for 1 hr at rt
2. customquenched with 1 mL ice-water
3. extractionThe resulted mixture was extracted with dichloromethane (20 mL×3)
4. dry with materialThe combined organic phases were dried over Na2SO4
5. concentrationconcentrated in vacuo

ORD record

ord-030c3bad5ed5426f8f560c1f7f9d4343

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293897B2