Boron trifluoride → HCID 66995201, compound

Temperature

-78 °C

2-Pyrrolidinone (4.47 g, 52.5 mmol) was mixed with THF (25 mL) and cooled to −78° C. Butyllithium (1.6 M in hexanes) (32.8 mL, 52.5 mmol) was added slowly then and the mixture was agitated for 10 minutes. Boron trifluoride ethereate (6.59 mL, 52.5 mmol) was added dropwise, followed by dropwise addition of epichlorohydrin (4.11 mL, 52.5 mmol). The resulting mixture was allowed to warm up overnight, then cooled and quenched with saturated sodium bicarbonate solution, and extracted 3 times with ethyl acetate. The extracts were washed with brine, dried and evaporated to give ˜4 g of crude oil. The crude oil was purified by chromatography on silica gel, eluting with 1-2% methanol/dichloromethane, to provide the title compound (1.53 g, 16.4% yield) as clear oil.

1. temperatureto warm up overnight
2. temperaturecooled
3. customquenched with saturated sodium bicarbonate solution
4. extractionextracted 3 times with ethyl acetate
5. washThe extracts were washed with brine
6. customdried
7. customevaporated
8. customto give ˜4 g of crude oil
9. customThe crude oil was purified by chromatography on silica gel
10. washeluting with 1-2% methanol/dichloromethane

ORD record

ord-7742c84e34c64660a523e51dd197e562

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022223B2