Hydroxyamine hydrochloride → 4-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

HRID 490393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490393
Cl.NO.[C:4]([SiH2:8][O:9][C:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:12]=[C:13]([CH:17]=O)[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5].CC1OC=CC=1CCO.[Cl-].ClC1N(C)C=C[N+:43]=1C>ClCCl.O.C(N(CC)CC)C>[C:4]([SiH2:8][O:9][C:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:12]=[C:13]([C:17]#[N:43])[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5]

Komponenten

8

Edukt 4

HCID 443297Hydroxyamine hydrochlorideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 184446362-(2-Methylfuran-3-yl)ethan-1-olHCID 1317274384-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde

Produkt 1

HCID 1317274374-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

Hydroxylamine hydrochloride (1.11 g, 16.0 mmoles) and triethylamine (2.22 ml) were added to a solution of 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde from (i)(6.3 g, 16.0 mmoles) in dichloromethane (125 ml) and the mixture was stirred at room temperature for 17 hours. After cooling to 0° C., 2-Chloro-1,3-dimethylimidazolium chloride (2.81 g, 16.6 mmoles) and triethylamine (4.6 ml) were added and the yellow suspension was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with dichloromethane. The combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water, and finally dried (MgSO4). The solvent was evaporated and the residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent) to afford 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile as a viscous oil, (3.75 g).

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. stirringthe yellow suspension was stirred at room temperature for 24 hours
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water
  5. dry with materialfinally dried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-658a3ba5fb3b4b63926eda0b5bc9e684
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528157B2

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