Water → 2-Acetoxy-4-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrile

HRID 1584360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584360
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH:25]=[O:26])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[C-:27]#[N:28].[Na+].[C:30]([O:33]C(=O)C)(=O)[CH3:31].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C:30]([O:26][CH:25]([CH2:24][CH2:23][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:27]#[N:28])(=[O:33])[CH3:31]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 212244623-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde

Produkt 1

HCID 212244242-Acetoxy-4-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde (1.79 g), sodium cyanide (0.3 g), acetic anhydride (0.62 g), benzyltributylammonium chloride (0.79 g), water (12 ml) and dichloromethane (35 ml) was stirred for 15 hours at room temperature. The organic layer was separated, which was washed with water and dried (MgSO4), followed by distilling off the solvent. The resulting oily product was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:3, v/v), was obtained 2-acetoxy-4-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]butyronitrile (2.0 g, 94%),

Aufarbeitung

  1. customThe organic layer was separated
  2. washwhich was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationby distilling off the solvent
  5. washFrom the fraction eluted with ethyl acetate-hexane (1:3

Quellen und Nachweise

ORD-Eintrag
ord-6179b7c9046844bdbc563fbefd86fec1
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932601

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