Imidazole → (E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

HRID 707673

Reaktionsgleichung

Reaktionsgleichung von HRID 707673
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].O>CN(C=O)C>[Si:12]([O:5][CH2:4]/[CH:3]=[CH:2]/[CH2:1][OH:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 175854trans-2-Butene-1,4-diol

Produkt 1

HCID 13841129(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-olAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2E)-2-butene-1,4-diol (8.22 mL, 0.10 mol) and imidazole (8.50 g, 0.125 mol) in DMF (50 mL) at 0° C., was added tert-butyldimethylsilyl chloride (7.50 g, 0.050 mol) in several portions over 10 minutes. The resulting mixture was warmed to room temperature and stirred (2 h), then poured into H2O (200 mL) and extracted with EtOAc (2×150 mL). The organic layer was washed (brine), dried (Na2SO4) and purified by silica gel column chromatography (hexanes:EtOAc) to yield 5 as a colorless oil (9.0 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 5.60-5.50 (m, 2H), 4.18 (m, 2H), 4.09 (m, 2H), 2.76 (br, 1H), 0.83 (s, 9H), 0.01 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 136.3, 135.4, 64.8, 63.8, 31.1, 23.6.

Aufarbeitung

  1. extractionextracted with EtOAc (2×150 mL)
  2. washThe organic layer was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. custompurified by silica gel column chromatography (hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4e446db5c6ca4c47a2c5d3010fa598b3
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175038B2

Verknüpfte Notizen

Wird geladen…