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Potassium Carbonate → 1-Methyl-2-(methylsulfanyl)benzene

HRID 2387302
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387302
[F:1][C:2]([F:27])([F:26])[C@@:3]([CH2:17][S:18][C:19]1[CH:24]=[CH:23][C:22](C)=[CH:21][CH:20]=1)([OH:16])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH3:15])([CH3:7])[CH3:6].F[B-](F)(F)F.[CH3:33][O+](C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O>[F:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C@:3]2([C:2]([F:27])([F:26])[F:1])[CH2:17][O:16]2)[CH:13]=1.[C:24]1([CH3:33])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:18][CH3:17]
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Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 58933188(S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Produkt 2

HCID 2597431-Methyl-2-(methylsulfanyl)benzeneAusbeute 20 %
HCID 11701812
(R)-2-[2-(5-Fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol (31.0 g, 77.0 mmol) in 200 mL of anhydrous dichloromethane was added trimethyloxonium tetrafluoroborate (17.2 g, 116 mmol). The resulting suspension was stirred at room temperature for 4.5 hours. A solution of potassium carbonate (K2CO3, 32.1 g, 232 mmol) in 200 mL of water was then added. After 19 hours, the reaction mixture was poured into 400 mL of saturated aqueous sodium bicarbonate solution and extracted with three 400 mL portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture can be used in the next step without reducing the yield or can be purified by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes) to afford (R)-2-[2-(5-fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane as a clear oil (23.2 g, contains 20% methyl tolyl thioether, 87%) which was used without further purification.

Aufarbeitung

  1. waitAfter 19 hours
  2. extractionextracted with three 400 mL portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customyield
  8. customcan be purified by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5c8a86299e4c466ba8168cf9827cf0aa
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268859B2

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