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

HRID 227449

反応式

HRID 227449 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4a4170c5aeee4106806b662e8d978de3
出典データセット
uspto-grants-2009_07
特許番号
US07560548B2

関連ノート

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