Formamide → 4-(4-Benzyloxyphenyl)oxazole

HRID 1030458Notes

Reaction equation

HRID 1030458 reaction equation
[CH:1]([NH2:3])=[O:2].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19]Br)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:3]=[CH:1][O:2][CH:19]=2)=[CH:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 516892Sodium BicarbonateHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 198202404-(4-Benzyloxyphenyl)oxazoleYield 16.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Formamide (1.0ml) was added to 4'-benzyloxy-2-bromoacetophenone (3.0g) and heated at 130° to 135° C. for 1 hour. Water was added to the reaction product, and the mixture was alkalified with aqueous solution of sodium bicarbonate and then extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline, treated with activated charcoal, dried with anhydrous sodium sulfate and then concentrated. The residue was purified by column chromatography on silica gel [eluting solvent: ethyl acetate-hexane (1:9)] to give 4-(4-benzyloxyphenyl) oxazole (410 mg, 16.6%). The product was further purified by recrystallization from diethyl etherhexane. m.p. 101°-102° C.

Workup

  1. temperatureheated at 130° to 135° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated saline
  4. additiontreated with activated charcoal
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel [eluting solvent: ethyl acetate-hexane (1:9)]

Sources & evidence

ORD record
ord-e5c51126a0444e85a45565fed0a2c96c
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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