Ethyl Acetate → 2-Hydroxy-1-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-ethanone

HRID 1005791ノート

反応式

HRID 1005791 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][OH:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25])([CH3:18])[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[OH:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:16]([CH3:18])[CH3:17])=[C:3]([C:12]([F:15])([F:14])[F:13])[CH:4]=1)=[O:11]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 219067681-(4-Fluoro-3-trifluoromethyl-phenyl)-2-hydroxy-ethanone

生成物 1

HCID 219067562-Hydroxy-1-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-ethanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Then 2-hydroxy-1-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-ethanone 28 was prepared as follows. To a solution of compound 27 (0.4 g, 1.8 mmole) and o-isopropylthiophenol (0.31 ml, 1.8 mmole) in DMF (10 ml) was added Cs2CO3 (0.59 g, 1.8 mmole). The mixture was stirred for 10 minutes and EtOAc (30 ml) was added. The mixture was filtered, concentrated and chromatographed on a silica gel column eluting with 30% EtOAc in hexane. The desired product 28 was obtained as an oil, 0.22 g, 34.8%. 1H-NMR (CDCl3, 300 MHz) δ 1.17 (d, J=7.0 Hz, 6 H), 3.40-3.46 (m, 2 H), 4.80 (s, 2H), 6.82 (d, J=8.4 Hz, 1H), 7.27-7.31 (m, 1H), 7.51-7.55 (m, 3H), 7.72 (d, J=8.4 Hz, 1H), 8.17 (s, 1H); MS (DCI/NH3) m/z 355 (M+H)+, 372 (M+NH4)+.

後処理

  1. customThen 2-hydroxy-1-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-ethanone 28 was prepared
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customchromatographed on a silica gel column
  5. washeluting with 30% EtOAc in hexane

出典と根拠

ORDレコード
ord-6322d4d2e9c045f8817eba39bc648cef
出典データセット
uspto-grants-2004_09
特許番号
US06787542B2

反応ノート

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