Dimethylformamide → Ethanone, 2-chloro-1-(3-furanyl)- (9CI)

Temperature

0 °C

Under N2, 3-furoic acid (25 g, 0.22 mmol) was dissolved in CH2Cl2 (200 mL) and DMF (few drops) then oxalyl chloride (23.9 mL, 0.27 mmol) was added at 0° C. The resulting solution was stirred at 0° C. for 15 min. and at r.t. for 30 min. The solvent was evaporated. To the acid chloride (3.1 g, 24 mmol) in Et2O (20 mL) at r.t. was added an ethereal solution of diazomethane until the reaction was completed by T.L.C. The reaction mixture was cooled to 0° C. and HCl (g) was bubbled in for 20 min.. Excess HCl (g) was removed by bubbling N2 into the solution for 2 h. The resulting solution was washed with a saturated solution of NaHCO3 (2×), brine, dried over MgSO4 and then concentrated. Flash chromatography of the residue with hexane:EtOAc 9:1 as eluent afforded the title compound as a white solid.

1. customThe solvent was evaporated
2. temperatureThe reaction mixture was cooled to 0° C.
3. customHCl (g) was bubbled in for 20 min.
4. customExcess HCl (g) was removed
5. customby bubbling N2 into the solution for 2 h
6. washThe resulting solution was washed with a saturated solution of NaHCO3 (2×), brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-601df1ceecc44671a18cf5de437905e5

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552437