1,4-Dioxane → HCID 23361366, Verbindung

HRID 233287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233287
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([CH:20]=[C:21]([C:27]#[N:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)[N:12]=1.O1CCOCC1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]([C:27]#[N:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:29][CH:30]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 54471283HCID 54471283, Verbindung

Produkt 1

HCID 23361366HCID 23361366, VerbindungAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]-α-cyanocinnamate (2.25 g) and dioxane (30 ml)--ethanol (30 ml) was added sodium borohydride (0.06 g) under ice-cooling. The mixture was stirred for one hour at the same temperature. The reaction mixture was poured into ice-water, which was made acid and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fractions eluted with chloroform-methanol (50:1, v/v), was obtained ethyl 3-[4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]phenyl]-2-cyanopropionate (2.25 g, quant.) as an oily product. NMR(δ ppm in CDCl3): 1.27(3H,t,J=7Hz), 2.39(3H,s), 3.00(2H,t,J=6.5Hz), 3.12(1H,dd,J=14&8Hz), 3.22(1H,dd,J=14&6Hz), 3.66(1H,dd,J=8&6Hz), 4.22(2H,q,J=7Hz), 4.24(2H,t,J=6.5Hz), 6.87(2H,d,J=9Hz), 7.17(2H,d,J=9Hz), 7.25-7.5(3H,m), 7.85-8.0(1H,m).

Aufarbeitung

  1. temperaturecooling
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. washFrom the fractions eluted with chloroform-methanol (50:1

Quellen und Nachweise

ORD-Eintrag
ord-d9adc0af8aed40079fabb92dd0acb956
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591862

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