1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one → 2-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol

HRID 916005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916005
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[CH2:20]([Mg]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([C:3]([OH:17])([CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6])[C:2]([F:1])([F:18])[F:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 178418336HCID 178418336, Verbindung

Produkt 1

HCID 102372232-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-olAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−70° C.) solution of 70 mg (0.25 mmol) of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (Example 1) in 2.5 mL of anhydrous THF was added a 2.0 M solution of benzyl magnesium chloride in THF. The mixture was stirred for 30 minutes and then was quenched with 15 mL of saturated aqueous ammonium chloride and extracted with five 5 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using hexanes to load the sample, and then eluted with hexanes and then EtOAc-hexanes (0.5:99.5, then 1:99) to afford 58 mg (62%) of the title compound as an oil.

Aufarbeitung

  1. customwas quenched with 15 mL of saturated aqueous ammonium chloride
  2. extractionextracted with five 5 mL portions of EtOAc
  3. washThe combined organic layers were washed with three 5 mL portions of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was chromatographed on silica gel
  8. washeluted with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a356144c643b45388e0d748faeb25e52
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268152B2

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