Cesium carbonate → 2-Hydroxy-4-(4-iodo-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeric acid methyl ester

HRID 1444471ノート

反応式

HRID 1444471 の反応式
[CH3:1][O:2][C:3](=[O:19])[C:4](=[O:18])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7].[F:20][C:21]([Si](C)(C)C)([F:23])[F:22].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:19])[C:4]([OH:18])([C:21]([F:23])([F:22])[F:20])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 686789254-(4-Iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid methyl ester

生成物 1

HCID 179892492-Hydroxy-4-(4-iodo-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeric acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

3 g of 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid (WO 98/54159) is added in a solution of 1.3 ml of thionyl chloride in 12 ml of methanol at 0° C. and stirred for 10 hours at room temperature. It is added to saturated bicarbonate solution and extracted with ethyl acetate. The organic phase is washed with bicarbonate solution and brine, dried (Na2SO4) and concentrated by evaporation. 3.2 g of 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid methyl ester is obtained as a crude product. This ester is mixed with 4.5 ml of trifluoromethyltrimethylsilane in 70 ml of DMF and 1.63 g of cesium carbonate at 0C and stirred for 10 hours at room temperature. 20 mg of tetrabutylammonium fluoride is added, and it is stirred for another 30 minutes at room temperature. The batch is added to water and extracted with ethyl acetate. The organic phase is washed with water and brine, dried (Na2SO4) and concentrated by-evaporation. After chromatography on silica gel (hexane/ethyl acetate 0->15%), 1.47 g of the title compound is obtained as a yellow oil.

後処理

  1. stirringit is stirred for another 30 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customby-evaporation

出典と根拠

ORDレコード
ord-0685708bb0104467b2ea36f13f72c039
出典データセット
uspto-grants-2010_02
特許番号
US07662821B2

反応ノート

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