Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

Methanesulfonyl chloride (18 mmol, 1.39 mL) was added to a flask containing (±)-tetrahydro-3-furanmethanol (1.53 g, 15.0 mmol) in tetrahydrofuran (25 mL) and triethylamine (3.13 mL, 22.5 mmol) at 0° C. under a nitrogen atmosphere. The cooling bath was removed and the reaction mixture was stirred overnight. A saturated solution of NaHCO3 (15 mL) was added to the reaction mixture followed by extraction with diethyl ether (3×15 mL). The combined organic extracts were dried over anhydrous magnesium sulfate. Filtration followed by concentration on a rotary evaporator yielded the product as a pale yellow solid (2.13 g) which was used in the next step without further purification.

1. customThe cooling bath was removed
2. additionA saturated solution of NaHCO3 (15 mL) was added to the reaction mixture
3. extractionfollowed by extraction with diethyl ether (3×15 mL)
4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
5. filtrationFiltration
6. concentrationfollowed by concentration on a rotary evaporator

ORD record

ord-56e82f5ede35450ca72218999f1dead0

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525065B1