(Trifluoromethyl)trimethylsilane → Ethyl-2-hydroxy-4-(2-methoxy-3-methylphenyl)-4-methyl-2-(trifluoromethyl)pentanoate

HRID 1443265노트

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HRID 1443265 반응식
[CH2:1]([O:3][C:4](=[O:20])[C:5](=[O:19])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])[CH3:2].[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]([OH:19])([C:22]([F:24])([F:23])[F:21])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])[CH3:2]

참가 물질

6

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 17989129Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate

생성물 1

HCID 17989264Ethyl-2-hydroxy-4-(2-methoxy-3-methylphenyl)-4-methyl-2-(trifluoromethyl)pentanoate수율 65.2%

시약·촉매·용매 2

HCID 2724141Tetrabutylammonium Fluoride촉매HCID 8028Tetrahydrofuran용매

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온도
35 °C

실험 절차

20 g (71.90) of ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate and 12.3 g (86.28 mmol) of (trifluoromethyl)trimethylsilane are introduced into 117 ml of tetrahydrofuran. At room temperature, 180 mg of tetrabutylammonium fluoride is added (heating to about 35° C.). After stirring overnight, 22.7 g (71.90 mmol) of tetrabutylammonium fluoride is added, and the batch is stirred for three hours at room temperature. After dilution with methyl tert-butyl ether, the organic phase is washed three times with water and once with brine. After the solvent is dried and spun off, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 16.33 g (65.2%) of the desired compound is isolated.

후처리

  1. stirringthe batch is stirred for three hours at room temperature
  2. washAfter dilution with methyl tert-butyl ether, the organic phase is washed three times with water
  3. customAfter the solvent is dried
  4. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-12382d8b585d490fa3b8087dbd488a15
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659297B2

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