Ethane, 2-bromo-1,1-diethoxy- → HCID 22911704, compound

HRID 1378447Notes

Reaction equation

HRID 1378447 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([NH2:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](OC(OCC)CBr)[CH3:19]>CN(C=O)C.O>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]1[O:16][CH:18]=[CH:19][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 123285482-(2-Phenoxyphenyl)acetamide

Product 1

HCID 22911704HCID 22911704, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-phenoxyphenyl)acetamide (3.9 g) and bromoacetaldehyde diethyl acetal (3.1 ml) in DMF (100 ml) was heated for 2 hours. After cooling, the resulting mixture was diluted with water and extracted with ether. The extracts were washed with water then dried, concentrated and chromatographed using ethyl acetate: hexane (50:50) as eluant to give 2-(2-phenoxyphenylmethyl)oxazole (1.77 g, 41%) as a brown oil, 1H NMR (CDCl3): delta 4.20 (2H,s), 7.01 (1H,s) and 7.54 (1H,s) ppm.

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washThe extracts were washed with water
  5. customthen dried
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-07443aed19d74bb1a8b194d82f4002c2
Source dataset
uspto-grants-1997_09
Patent number
US05668160

Reaction notes

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