Imidazole → Ethyl 4-cyano-3-(tert-butyldiphenylsilyloxy)-butanoate

HRID 226273

Reaktionsgleichung

Reaktionsgleichung von HRID 226273
N1C=CN=C1.[C:6]([CH2:8][CH:9]([OH:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:7].[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].O>ClCCl>[C:6]([CH2:8][CH:9]([O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:7]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 4184461Ethyl 4-cyano-3-hydroxybutanoate

Produkt 1

HCID 11718177Ethyl 4-cyano-3-(tert-butyldiphenylsilyloxy)-butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Imidazole (6.5 g, 0.095 mol) was added to a chilled solution (−5 to −10° C.) of ethyl 4-cyano-3-hydroxybutanoate (10 g, 0.063 mol) in dichloromethane (100 ml) under stirring, followed by tert-butyl diphenyl silyl chloride (15.7 g, 0.057 mol). After stirring for 4 hours at room temperature, water (250 ml) was added to the reaction mixture and layers separated. The aqueous layer was extracted with dichloromethane (100 ml) and combined with the organic layer. The combined organic layer was evaporated to give title compound.

Aufarbeitung

  1. stirringAfter stirring for 4 hours at room temperature
  2. customseparated
  3. extractionThe aqueous layer was extracted with dichloromethane (100 ml)
  4. customThe combined organic layer was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e26669bfbe024d138ddc363d0ea73067
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557238B2

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