(3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol → Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-

HRID 1049404

Reaktionsgleichung

Reaktionsgleichung von HRID 1049404
[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[O-2].[Mn+4].[O-2]>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[CH:26]=[O:27])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 1

HCID 57049439(3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol

Produkt 1

HCID 10883279Benzaldehyde, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-Ausbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)methanol (6.96 g) in THF (37 mL) was added manganese(IV) oxide (8.03 g), and the mixture was stirred at room temperature for 5.5 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.61 g) as a pale-yellow oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d468fae0eea74f0eae0320f6c0260089
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382188B2

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