Lithium Chloride → [2-(4-Fluorophenyl)-1,3-oxazolin-4-yl]methan-1-ol

Methyl 2-(4-fluorophenyl)-1,3-oxazoline-4-carboxylate (1.0 g, 4.5 mmol) was dissolved in 30 ml of absolute ethanol. To this solution was added lithium chloride (0.380 g, 9.0 mmol) and sodium borohydride (0.342 g, 9.0 mmol). The reaction was stirred at room temperature until starting material was consumed (TLC, 15:1 dichloromethane:methanol). Ethanol was removed under reduced pressure and replaced with 35 ml of water. The aqueous solution was acidified to about pH 2 with concentrated HCl, and the acidic solution extracted with ethyl acetate (3×50 ml). The resulting organic layer was washed with water (3×50 ml) and dried with sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue purified using column chromatography (3% MeOH in DCM) to yield [2-(4-fluorophenyl)-1,3-oxazolin-4-yl]methan-1-ol (600 mg, M+1=196.1).

1. customwas consumed (TLC, 15:1 dichloromethane:methanol)
2. customEthanol was removed under reduced pressure
3. extractionthe acidic solution extracted with ethyl acetate (3×50 ml)
4. washThe resulting organic layer was washed with water (3×50 ml)
5. dry with materialdried with sodium sulfate
6. concentrationThe organic layer was concentrated under reduced pressure
7. customthe residue purified

ORD record

ord-25654008388b458f9e3fa266ffabfc28

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026321B2