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Potassium Carbonate → (R)-5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)-ethyl]-2,3-dihydrobenzofuran

HRID 854170
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 854170
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:29])([CH3:28])[CH2:12][C@:13]([CH2:19]SC2C=CC(C)=CC=2)([OH:18])[C:14]([F:17])([F:16])[F:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.F[B-](F)(F)F.C[O+](C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:28])([CH3:29])[CH2:12][C@:13]2([C:14]([F:17])([F:15])[F:16])[CH2:19][O:18]2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 69419561(S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Produkt 1

HCID 11638349(R)-5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)-ethyl]-2,3-dihydrobenzofuran
Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol (1.43 g, 3.21 mmol) in 10 mL of anhydrous dichloromethane was added trimethyloxonium tetrafluoroborate (713 mg, 4.82 mmol). The resulting suspension was stirred at room temperature for 4.5 hours. A solution of potassium carbonate (1.33 g, 9.64 mmol) in 10 mL of water was then added. After 13 hours, the reaction mixture was poured into 40 mL of saturated aqueous sodium bicarbonate solution and extracted with three 50 mL portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes) afforded the title compound as a clear oil (974 mg, 95%).

Aufarbeitung

  1. waitAfter 13 hours
  2. extractionextracted with three 50 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. customPurification by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-899c0cdea39447fc91ae5270a8c98a3f
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07256300B2

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