Cerium(III) chloride → 3-(2-Fluoropyridin-3-YL)cyclopent-2-enol

A solution of 3-(2-fluoropyridin-3-yl)cyclopent-2-enone (1582 mg, 8.93 mmol) in Tetrahydrofuran (20 mL) and Methanol (20 mL) was cooled to 0° C. under nitrogen. Cerium (III) chloride (2201 mg, 8.93 mmol) was added, followed by sodium borohydrate (676 mg, 17.86 mmol) in 4 lots, over 15 min. After 30 min, the reaction was quenched with saturated ammonium chloride solution (20 mL—effervescence!), and partitioned between dichloromethane (100 mL) and saturated ammonium chloride solution (30 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, dried over MgSO4, and concentrated, affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 180.1 (M+1).

1. customthe reaction was quenched with saturated ammonium chloride solution (20 mL—effervescence!)
2. custompartitioned between dichloromethane (100 mL) and saturated ammonium chloride solution (30 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD record

ord-8ac9c53982f94aeaac22018e779191cc

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318718B2