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

HRID 1005791노트

반응식

HRID 1005791 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-6322d4d2e9c045f8817eba39bc648cef
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787542B2

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