Acetic Acid → HCID 70655087, compound

Temperature

23 °C

A solution of benzylamine (1.26 mL, 11.6 mmol) in methanol (2 mL) was added drop wise to a refluxing solution of dihydro-furan-3-one (1 g, 11.6 mmol), paraformaldehyde (1.04 g, 34.84 mmol), and glacial acetic acid (0.67 mL, 11.61 mmol) in methanol (8 mL) over a period of 3 hours under nitrogen. Reflux was continued for 1 hour after which, the brown reaction mixture was stirred at 23° C. for 16 hours. The reaction mixture was concentrated in vacuo. The resulting oil was diluted with water and basified with 6 N aqueous NaOH solution. The aqueous solution was extracted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel with 25-30% ethyl acetate in hexane as eluent. The title compound was obtained as a colorless sticky liquid (500 mg, 20%).

1. temperatureReflux
2. concentrationThe reaction mixture was concentrated in vacuo
3. additionThe resulting oil was diluted with water
4. extractionThe aqueous solution was extracted with ethyl acetate
5. washwashed with water, brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by flash column chromatography on silica gel with 25-30% ethyl acetate in hexane as eluent

ORD record

ord-56572150939e4bc09259ca21638b1a1d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703763B2