Styrene Oxide → 2-[2-Methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol

HRID 346849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346849
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:20][Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:22][CH3:23])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=2)[NH:3]1.[C:28]1([CH:34]2[CH2:36][O:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl([O-])(=O)(=O)=O.[Li+].[NH4+].[Cl-]>C(#N)C.CCOCC>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:20][Si:21]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:26][CH3:27])([C:12]([F:15])([F:14])[F:13])[C:16]([F:17])([F:18])[F:19])[CH:8]=2)[N:3]1[CH:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:36][OH:35]

Komponenten

7

Edukt 4

HCID 7276Styrene OxideHCID 25517Ammonium ChlorideHCID 210822122-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indoleHCID 23665649Lithium perchlorate

Produkt 1

HCID 210822072-[2-Methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanolAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 114 mg (0.275 mmol) of 2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole (example 51.2) in 1 mL of acetonitrile were added 0.063 mL (0.55 mmol) of racemic phenyloxirane and 58 mg (55 mmol) of lithiumperchlorate. After stirring at 80° C. for 18 hrs, the mixture was distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 4:1 yielded 77 mg (52%) of 2-[2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol, MS: 534 (MH+).

Aufarbeitung

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-39c5ce7bf222446787f9bac80aaaa14d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173048B2

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