Water → 4-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

HRID 1173039

反応式

HRID 1173039 の反応式
Cl[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH3:7][C:5]1[N:6]=[C:2]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium Carbonate2 回HCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester収率 56%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
65 °C

実験手順

To a solution of ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate (X-1) (0.25 g, 1.22 mmol) and phenol (0.15 g, 1.61 mmol) in acetone (3 mL) was added K2CO3 (0.25 g, 1.81 mmol). The mixture was heated for 18 h at 65° C. Additional K2CO3 (0.25 g) was added and the mixture was continued to heat at 70° C. for 24 h. Upon cooling, water was added (10 mL). The mixture was extracted with Et2O. The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a white solid (0.18 g, 56%). 1H NMR (CDCl3) δ 7.44 (m, 2H), 7.33-7.27 (m, 3H), 4.26 (q, J=7.1 Hz, 2H), 2.60 (s, 3H), 1.31 (t, J=7.1 Hz, 3H).

後処理

  1. temperatureto heat at 70° C. for 24 h
  2. temperatureUpon cooling
  3. extractionThe mixture was extracted with Et2O
  4. dry with materialThe combined organics were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1ab957b567864ee187c01177daca1b3e
出典データセット
uspto-grants-2010_11
特許番号
US07834013B2

関連ノート

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