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

HRID 1173039

반응식

HRID 1173039 반응식
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]

참가 물질

6

반응물 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium Carbonate2회HCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1ab957b567864ee187c01177daca1b3e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834013B2

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