4-Fluorobenzamide → Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate

HRID 227449

반응식

HRID 227449 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH:12]([CH3:21])[C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][C:12]=1[CH3:21])[CH3:19]

참가 물질

4

반응물 2

HCID 715724-FluorobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

생성물 1

HCID 85817159Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate수율 48.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
140 °C

실험 절차

A suspension of 4fluorobenzamide (12.9 g) and ethyl 4bromo-3-oxopentanoate (Chem Abs No. 3618769-6; 5.24 g) in anhydrous toluene (120 ml) was heated at 140° C. for 19 h, using a Dean-Stark trap. The solution was allowed to cool, filtered, and the residual solid washed with toluene (30 ml). The combined filtrate and washings were concentrated in vacuo to give a brown oil, which was purified by Biotage flash chromatography on silica gel (90 g column), eluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90), to give the title compound as a yellow solid (2.98 g).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. washthe residual solid washed with toluene (30 ml)
  4. concentrationThe combined filtrate and washings were concentrated in vacuo
  5. customto give a brown oil, which
  6. customwas purified by Biotage flash chromatography on silica gel (90 g column)
  7. washeluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90)

출처 및 근거

ORD 기록
ord-4a4170c5aeee4106806b662e8d978de3
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560548B2

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