Ammonium Acetate → HCID 22723464, compound

HRID 1272194Notes

Reaction equation

HRID 1272194 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[CH:19]([O-:21])=O.[Na+].C([O-])(=O)C.[NH4+:27]>CN(C)C=O.O>[CH2:12]([O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:27]=[CH:19][O:21][CH:2]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 2723810Sodium FormateHCID 125418501-[2-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 22723464HCID 22723464, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1a97bb534e7e40279eb7ea4052ada2b7
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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