1,2-Dichloroethane → Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylate

HRID 270152

반응식

HRID 270152 반응식
[Si:1]([O:18][CH2:19][C:20](=O)[CH:21](Cl)[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH2:37])=[S:36])=[CH:33][CH:32]=1.ClCCCl.O>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[N:37]=[C:35]([C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:40])([F:29])[F:41])=[CH:39][CH:38]=2)[S:36][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 27348234-(Trifluoromethyl)thiobenzamideHCID 17951839Ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}2-chloro-3-oxobutanoate

생성물 1

HCID 17951800Ethyl 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazole-5-carboxylate수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 500ml round-bottom flask equipped with a magnetic stir-bar was mixed ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-chloro-3-oxobutanoate (20.4g, 52.88mmoles, 1eq), 4-trifluoromethylthiobenzamide (12.2g, 59.5mmoles, 1.1eq), 1,2-dichloroethane (150ml, 0.44M) and H2O (3ml). This mixture was refluxed for 12hrs. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2(100ml) and washed with sat. NaHCO3. Once the phases were separated, the organic phase washed with water, brine and dried over Na2SO4. This was then filtered, concentrated in vacuo and purified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes) to yield 20.3g (76%) of the titled compound.

후처리

  1. customTo a 500ml round-bottom flask equipped with a magnetic stir-bar
  2. temperatureThis mixture was refluxed for 12hrs
  3. washwashed with sat. NaHCO3
  4. customOnce the phases were separated
  5. washthe organic phase washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationThis was then filtered
  8. concentrationconcentrated in vacuo
  9. custompurified via silica gel chromatography (5% EtOAc/Hexanes to 20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-c69fbdd2ad324f929bc0c46723c1d169
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449468B2

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