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Diisobutylaluminumhydride → [2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

HRID 1176545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1176545
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([C:33](OC)=[O:34])[C:18]=2[N:17]=1>O1CCCC1>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][OH:34])[C:18]=2[N:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 68502641Methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate

Produkt 1

HCID 68503680[2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

35 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at −70° C. to a solution of 4.95 g of methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate in 200 ml of tetrahydrofuran. The reaction mixture is then stirred at −10° C. for 1 hour and subsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase is washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The combined aqueous phases are reextracted with ethyl acetate (3×)—the combined organic phases are washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residues by means of flash chromatography (SiO2 60F). Rf=0.21 (95:5 ethyl acetate-methanol); Rt=3.91.

Aufarbeitung

  1. customsubsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase
  2. washis washed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. washare washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-fc4d1b89c33f45a885cd14b23d8a19e4
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842688B2

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