3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

HRID 445035

Reaktionsgleichung

Reaktionsgleichung von HRID 445035
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].N1C=CN=C1>C(Cl)(Cl)Cl>[C:1]([Si:5]([CH3:8])([CH3:7])[O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1013-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehydeAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

t-Butyldimethylchlorosilane (26.01 g; 172.56 mmol) was added to a solution of 3-hydroxybenzaldehyde (20.7 g; 164.35 mmol) and imidazole (27.97 g; 410.9 mmol) in CHCl3 (300 mL) at 0° C. via a funnel. The reaction was stirred under N2 overnight while it warmed to room temperature. The reaction mixture was washed by water (100 mL×3) and brine (100 mL×1), dried over Na2SO4 and concentrated to give crude product (29.56 g), which was purified by column chromatography eluted by (i) pentane and (ii) 3% EtOAc in pentane to give 3-(t-butyl-dimethyl-silanyloxy)-benzaldehyde (21 g; 54%). 1H NMR (300 MHz, CDCl3) δ 9.93 (s, 1H), 7.45 (d, 1H, J=7.5 Hz), 7.38 (dd, 1H, J=7.5, 7.5 Hz), 7.31 (d, 1H, J=1.0 Hz), 7.09 (1H, dd, J=7.5, 1.0 Hz), 0.98 (s, 9H), 0.20 (s, 6H).

Aufarbeitung

  1. washThe reaction mixture was washed by water (100 mL×3) and brine (100 mL×1)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product (29.56 g), which
  5. customwas purified by column chromatography
  6. washeluted by (i) pentane and (ii) 3% EtOAc in pentane

Quellen und Nachweise

ORD-Eintrag
ord-4c8d5becb1184b82ac20379c999b5122
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476280B2

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