Benzamide → Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate

HRID 4399

反応式

HRID 4399 の反応式
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>>[C:2]1([C:1]2[O:8][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 2331BenzamideHCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium Bicarbonate

生成物 1

HCID 15567335Ethyl (2-phenyl-1,3-oxazol-4-yl)acetate収率 38%

反応条件

温度
120 °C

実験手順

A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9) to yield ethyl 2-phenyl-4-oxazoleacetate as an oil (26.4 g, 28.0%). NMR (CDCl3)δ: 1.27 (3H, t, J=7 Hz), 3.68 (3H, s), 4.15 (2H, q, J=7 Hz), 7.4 (3H, m), 7.67 (1H, s), 8.0 (2H, m).

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with ethyl ether-hexane (1:9)

出典と根拠

ORDレコード
ord-e63f4e4c221e4ca7857dee83451d2403
出典データセット
uspto-grants-1988_02
特許番号
US04725610

関連ノート

読み込み中…