Dichloromethane → 1-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-one

HRID 1662563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662563
[Si:1]([O:8][C:9]1[C:10]([F:20])=[C:11]([CH:16]([OH:19])[CH2:17][CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CCOC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[Si:1]([O:8][C:9]1[C:10]([F:20])=[C:11]([C:16](=[O:19])[CH2:17][CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 12217721Iodo benzene diacetateHCID 577069101-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-ol

Produkt 1

HCID 577063781-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724126TempoKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 200 mL round bottom flask was charged with 90.C (0.48 g, 1.6 mmol), DCM (15 mL), iodobenzene diacetate (0.56 g, 1.7 mmol), and TEMPO (0.012 g, 0.079 mmol). The mixture was stirred overnight at room temperature and diluted with EtOAc. The organics were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 90.D (0.45 g, 94% yield) as a colorless oil.

Aufarbeitung

  1. washThe organics were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f33779ab823d447c906d34157bd2ab42
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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