Sodium borohydride → HCID 13714726, Verbindung

HRID 65093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65093
[C:1]([C:3]([CH:20]([CH3:22])[CH3:21])([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1)[CH2:4][CH2:5][CH:6]=O)#[N:2].[N+:23]([C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[O:28][CH2:29][CH2:30][CH2:31][NH2:32])([O-:25])=[O:24].[BH4-].[Na+]>CO>[CH:20]([C:3]([C:8]1[CH:9]=[C:10]([O:18][CH3:19])[C:11]([O:16][CH3:17])=[C:12]([O:14][CH3:15])[CH:13]=1)([CH2:4][CH2:5][CH2:6][NH:32][CH2:31][CH2:30][CH2:29][O:28][C:27]1[CH:33]=[CH:34][CH:35]=[CH:36][C:26]=1[N+:23]([O-:25])=[O:24])[C:1]#[N:2])([CH3:21])[CH3:22]

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 52768743-(2-Nitrophenoxy)propylamineHCID 14000643HCID 14000643, Verbindung

Produkt 1

HCID 13714726HCID 13714726, VerbindungAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 8.09 g of 4-cyano-4-isopropyl-4-(3,4,5-trimethoxyphenyl)butyraldehyde and 4.96 g of 3-(2-nitrophenoxy)-propylamine in 100 ml of methanol was refluxed for 3 hours. After cooling, to the solution was added 0.50 g of sodium borohydride and the solution was stirred overnight at room temperature. The solvent was removed and to the residue was added water. The solution was extracted with chloroform and the extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent to give 6.48 g of the desired compound as a pale yellow oil.

Aufarbeitung

  1. temperatureAfter cooling, to the solution
  2. customThe solvent was removed and to the residue
  3. additionwas added water
  4. extractionThe solution was extracted with chloroform
  5. washthe extract was washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel using 10% methanol-chloroform as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-285edd3b3abc4dd997fce3177e670764
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612329

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