Oxazole → Ethyl 2-(4'-hydroxyphenyl)-1,3-oxazole-4-carboxylate

HRID 1458405ノート

反応式

HRID 1458405 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].O1C=CN=C1>C(OCC)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:8]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 9255OxazoleHCID 650524-HydroxybenzamideHCID 66144Ethyl bromopyruvate

生成物 1

HCID 2758854Ethyl 2-(4'-hydroxyphenyl)-1,3-oxazole-4-carboxylate収率 87%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
115 °C

実験手順

A mixture of 25.0 g (182.3 mmol) of 4-hydroxybenzamide and 23.0 mL (182.3 mmol) of ethyl bromopyruvate was stirred and heated at 115° C. for 30 minutes. The mixture cooled to room temperature and sat under N2 atmosphere overnight. Ethyl acetate (100 mL) was added and the mixture stirred for 1 hour. The solid oxazole (36.99 g, 158.6 mmol) was collected by suction filtration in 87% yield: 1H NMR (CDCl3) δ 10.21 (broad s, 1H), 8.82 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 4.29 (q, 2H), 1.29 (t, 3H); IR (cm-1) 3400, 3169, 1731, 1612, 1731, 1507, 1444; FDMS 233. Anal. (C12H11NO4) C, H, N.

後処理

  1. temperatureThe mixture cooled to room temperature
  2. stirringthe mixture stirred for 1 hour

出典と根拠

ORDレコード
ord-8708cdaba2654d0593427759120ceee9
出典データセット
uspto-grants-1998_12
特許番号
US05849766

反応ノート

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