Dichloromethane → 2-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile

HRID 977244

Reaktionsgleichung

Reaktionsgleichung von HRID 977244
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=[O:26])=[CH:19][CH:18]=1)=[O:16].[C-:27]#[N:28].[Na+].[C:30]([O:33]C(=O)C)(=O)[CH3:31].ClCCl>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[C:30]([O:26][CH:25]([CH2:24][CH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:15](=[O:16])[CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:22][CH:21]=1)[C:27]#[N:28])(=[O:33])[CH3:31]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 199656273-[4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propionaldehyde

Produkt 1

HCID 199656432-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrileAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propionaldehyde (1.47 g), sodium cyanide (0.25 g), acetic anhydride (0.52 g), benzyltributylammonium chloride [(C4H9)3 (C6H5CH2)N+Cl- ](0.66 g) and dichloromethane (30 ml)- water (10 ml) was stirred at room temperature for 18 hours. The organic layer was separated, washed with water, dried (MgSO4) and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2), 2-acetoxy-4-[4-[3-(5-methyl- 2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile (1.75 g, quantitative) was obtained as an oily substance. NMR (δ ppm in CDCl3): 2.13 (3H, s), 2.15-2.3 (2H, m), 2.38 (3H, s), 2.8-3.0 (4H, m), 3.39 (2H, t, J=7 Hz), 5.29 (1H, t, J=6.5 Hz), 7.28 (2H, d, J=8 Hz), 7.35-7.5 (3H, m), 7.9-8.05 (4H, m)

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with ethyl acetate-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-c8edab1bf1d841d89251980e8e93f5cf
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614544

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