Ammonium Acetate → HCID 22723464, Verbindung

A mixture of 2-bromo-1-(2-benzyloxyphenyl)ethanone (J. Med. Chem., 35:3045, 1992; 10.0 g, 32.77 mmol) and sodium formate (4.46 g, 65.6 mmol) in dry dimethylformamide (100 ml) is stirred at room temperature overnight. The mixture is poured into water (400 ml) and extracted with dichloromethane (2×100 ml). The combined extracts are dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in acetic acid (100 ml), treated with ammonium acetate (12.62 g, 163.7 mmol), and the mixture is heated for 3 hours. After cooling, the mixture is diluted with water (400 ml) and extracted with dichloromethane (2×100 ml). The combined organic layers are washed with saturated aqueous sodium bicarbonate solution (2×100 ml), dried over sodium sulfate, and concentrated in vacuo. 4-(2-Benzyloxyphenyl)oxazole (1.99 g, 24%) is obtained after chromatography (silica gel, dichloromethane).

1. extractionextracted with dichloromethane (2×100 ml)
2. dry with materialThe combined extracts are dried over sodium sulfate
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue is dissolved in acetic acid (100 ml)
5. temperaturethe mixture is heated for 3 hours
6. temperatureAfter cooling
7. extractionextracted with dichloromethane (2×100 ml)
8. washThe combined organic layers are washed with saturated aqueous sodium bicarbonate solution (2×100 ml)
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo

ORD-Eintrag

ord-1a97bb534e7e40279eb7ea4052ada2b7

Quelldatensatz

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07208505B2