Tetrahydrofurfuryl alcohol → (Tetrahydrofuran-2-yl)methyl methanesulfonate

Temperature

0 °C

Tetrahydrofurfuryl alcohol (2.01 g, 19.7 mmol, 1.0 eq.) was dissolved in dichloromethane (100 mL) under an argon atmosphere, cooled to 0° C. and treated sequentially with triethylamine (3.02 mL, 21.7 mmol, 1.1 eq) and methanesulfonyl chloride (1.60 mL, 20.7 mmol, 1.05 eq.). The ice bath was removed and stirring continued for 14 h before the mixture was poured into a separatory funnel containing water. The phases were separated and the organic layer was washed with water (4×), dried on MgSO4, filtered and concentrated in vacuo to yield 3.26 g [92%] of tetrahydrofurfuryl methanesulfonate as a crude pale yellow oil, used in the subsequent displacement step without purification.

1. customThe ice bath was removed
2. additionwas poured into a separatory funnel
3. additioncontaining water
4. customThe phases were separated
5. washthe organic layer was washed with water (4×)
6. customdried on MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-72aac5e214b64d28bf5983b6320d93b9

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037916B2