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

HRID 1443265ノート

反応式

HRID 1443265 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2724141Tetrabutylammonium Fluoride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-12382d8b585d490fa3b8087dbd488a15
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

反応ノート

読み込み中…