1,2-Dichloroethane → (3-{1-Methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethylsulfanyl}-phenyl)-acetic Acid Methyl Ester

HRID 860683

반응식

HRID 860683 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[O:5][C:6]=1[C:7](O)([CH3:9])[CH3:8].[CH3:21][O:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([SH:31])[CH:26]=1.ClCCCl>C(OCC)(=O)C.[I-].[Zn+]>[CH3:21][O:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([S:31][C:7]([CH3:9])([C:6]2[O:5][C:4]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[N:3][C:2]=2[CH3:1])[CH3:8])[CH:26]=1

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 14820216Methyl 2-(3-mercaptophenyl)acetateHCID 695893092-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol

생성물 1

HCID 69589602(3-{1-Methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethylsulfanyl}-phenyl)-acetic Acid Methyl Ester

시약·촉매·용매 2

HCID 178506616HCID 178506616, 화합물촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol (0.1 g, 0.351 mmol), (3-Mercapto-phenyl)-acetic acid methyl ester (0.070 g, 0.386 mmol), zinc (I) iodide (0.056 g, 0.176 mmol), and 1,2-dichloroethane (2 mL) is stirred at room temperature 24 hr. The reaction mixture is diluted with ethyl acetate (25 mL), and washed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each), dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 8:2 hexanes:ethyl acetate to afford the product as a colorless film, 0.105 g, 66%. MS M++1 286. The structure is confirmed by 1H NMR spectroscopy.

후처리

  1. washwashed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via silica chromatography
  6. washeluting with 8:2 hexanes
  7. customethyl acetate to afford the product as a colorless film, 0.105 g, 66%

출처 및 근거

ORD 기록
ord-bab5aa22367e45bea9b2e2480dc93bae
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153878B2

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