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

HRID 1005791

Reaktionsgleichung

Reaktionsgleichung von HRID 1005791
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6322d4d2e9c045f8817eba39bc648cef
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787542B2

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