Water → HCID 15097264, compound

Methanesulfonyl chloride (17.9 mL, 232 mmol) was added dropwise to a solution of (5,6-dihydro-4H-pyran-2-yl)methanol (25.51 g, 193 mmol) [see Synlett, Vol. 5, p. 533 (1997)] and triethylamine (40.4 mL, 290 mmol) in dichloromethane (600 mL) under salt ice cooling over 15 minutes. After stirring at the same temperature for two hours, triethylamine (18.8 mL, 135 mmol) and methanesulfonyl chloride (7.5 mL, 97 mmol) were added, and the mixture was further stirred for 30 minutes. Water (300 mL) was added to the reaction solution, followed by extraction with ethyl acetate (1.5 L). The resulting organic layer was washed with water (300 mL) and brine (300 mL). The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting crude title compound was used for the next reaction without purification.

1. stirringthe mixture was further stirred for 30 minutes
2. extractionfollowed by extraction with ethyl acetate (1.5 L)
3. washThe resulting organic layer was washed with water (300 mL) and brine (300 mL)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure
7. customThe resulting crude title compound was used for the next reaction without purification

ORD record

ord-723f0aedfb7e4e27935e6ec3156f7ef9

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2