Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

To a stirring solution of (3-oxolanyl)methan-1-ol (25 g, 245 mmol) and triethylamine (34.37 mL, 245 mmol) in dry dichloromethane (250 mL) at 0° C. under N2 atmosphere was added dropwise methanesulfonyl chloride (18.94 mL, 245 mmol). The reaction mixture was stirred overnight after warming to room temperature, then a saturated solution of NaHCO3 (100 mL) was added and the mixture stirred for another 30 min. The biphasic mixture was separated and the organic layer was discarded. The aqueous layer was extracted with dichloromethane (3×25 mL) and the combined dichloromethane extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give 42.16 g of (3-oxolanyl)methyl methanesulfonate (99%) as a light brown liquid.

1. stirringthe mixture stirred for another 30 min
2. customThe biphasic mixture was separated
3. extractionThe aqueous layer was extracted with dichloromethane (3×25 mL)
4. dry with materialthe combined dichloromethane extracts were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation

ORD record

ord-7b7b02f049a445cd80eeecc854fcb6ec

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06956042B2