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

HRID 1584360Notes

Reaction equation

HRID 1584360 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

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%),

Workup

  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

Sources & evidence

ORD record
ord-6179b7c9046844bdbc563fbefd86fec1
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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