4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 279232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279232
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C.CCOC(C)=O>[Si:15]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3) 4-Hydroxybenzaldehyde (20 g, 0.164 mol) was dissolved in DMF (60 ml) and stirred at RT as imidazole (22.3 g, 0.328 mol) and tert-butyldimethylsilyl chloride (32.1 g, 0.213 mol) were added. The reaction mixture was stirred for 16 h. The solution was diluted with EtOAc, washed with water, brine, then dried (MgSO4) and concentrated in-vacuo to afford 24 g of crude 4-(tert-butyldimethylsilanyloxy)benzaldehyde.

Aufarbeitung

  1. additionwere added
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2e1c3176a6ef478a84e23df04e7e17ae
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362217B1

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