Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)-1-fluoroethyl)benzaldehyde

HRID 1689289

Reaktionsgleichung

Reaktionsgleichung von HRID 1689289
Br[C:2]1[CH:3]=[C:4]([CH:8]([F:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>C1COCC1>[Si:11]([O:10][CH2:9][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:26]=[O:27])[F:18])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 57989324(2-(3-Bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 579892013-(2-(tert-Butyldimethylsilyloxy)-1-fluoroethyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of (2-(3-bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilane (example 39, step c) (1.8 g) in THF (36 mL) was cooled to −78° C. under an atmosphere of nitrogen and treated with butyllithium (1.8M in hexanes, 3.3 mL), added dropwise over 5 minutes. The solution was stirred at −78° C. for 30 minutes, treated with N,N-dimethylformamide (0.63 mL), stirred at −78° C. for a further 30 minutes, then removed from the cooling bath and allowed to warm to room temperature over 140 minutes. The solution was quenched by the addition of 10% aqueous ammonium chloride, and the resulting mixture was extracted twice with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 50% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 1.26 g.

Aufarbeitung

  1. additionadded dropwise over 5 minutes
  2. stirringstirred at −78° C. for a further 30 minutes
  3. customremoved from the cooling bath
  4. temperatureto warm to room temperature over 140 minutes
  5. customThe solution was quenched by the addition of 10% aqueous ammonium chloride
  6. extractionthe resulting mixture was extracted twice with diethyl ether
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous magnesium sulphate
  9. custompurified by flash chromatography on silica
  10. washeluted with 50% dichloromethane in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-70ccd8263d074370b4a469ecc1e30aac
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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