Water → 4-Phenyl-1,3-oxazole

HRID 2399913

반응식

HRID 2399913 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([O-:13])=O.[NH4+:14].O>C(O)=O>[C:5]1([C:3]2[N:14]=[CH:11][O:13][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 2723923Ammonium formate

생성물 1

HCID 5892794-Phenyl-1,3-oxazole수율 31%

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

A mixture of 2-bromoacetophenone and ammonium formate in formic acid was stirred at reflux under nitrogen for 2 hours. The cooled reaction mixture was treated with 400 mL of H2O and extracted with ether (3×200 mL). The combined organics were washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9) to afford 8.9 g (31%) of 4-phenyloxazole as a yellow oil.

후처리

  1. temperatureat reflux under nitrogen for 2 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (3×200 mL)
  4. washThe combined organics were washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9)

출처 및 근거

ORD 기록
ord-d210e6dcc0614ccab50e24bcaaf1dcbc
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05451686

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