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

HRID 977244Notes

Reaction equation

HRID 977244 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 199656432-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrileYield 99.3%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-c8edab1bf1d841d89251980e8e93f5cf
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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