Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → HCID 18952387, Verbindung

HRID 1492307

Reaktionsgleichung

Reaktionsgleichung von HRID 1492307
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH:20]=[CH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH2:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate

Produkt 1

HCID 18952387HCID 18952387, VerbindungAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate (14.4 g) (obtained as described in International patent application, publication no. WO 91/11999) in methanol (280 ml) was catalytically hydrogenated over 10% palladium on carbon (2.9 g) at 3 atmospheres pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:3 v/v), to give methyl 4-(t-butyldimethylsilyloxy)-3-propylbenzoate (B) (11.7 g) as an oil; NMR: 0.25(s, 6H), 0.95(t, 3H), 1.0(s, 9H), 1.5-1.7(m, 2H), 2.6(t, 2H), 3.9(s, 3H), 6.8(d, 1H), 7.8(dd, 1H), 7.8(s, 1H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate/hexane (1:3 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-86da75fd7f49456cb8a013750c1e6a8a
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05373015

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