Phenylacetonitrile → 5-(2-Methyl-1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazole

HRID 1380007Notes

Reaction equation

HRID 1380007 reaction equation
[C:1]1([CH2:7][C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][C:11]1([C:16]2[CH:21]=C[C:19]([N+:22]([O-])=[O:23])=[CH:18][CH:17]=2)[O:15][CH2:14][CH2:13][O:12]1.[OH-].[Na+]>CO>[CH3:10][C:11]1([C:16]2[CH:17]=[CH:18][C:19]3[C:8]([CH:21]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:23][N:22]=3)[O:12][CH2:13][CH2:14][O:15]1

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 6497105-(2-Methyl-1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylacetonitrile (0.84 g, 7.2 m mol) and 2-methyl-2-(4-nitrophenyl)-1,3-dioxolane (mp. 69°-71° C.) (1.50 g, 7.2 m mol) were added to a room temperature solution of sodium hydroxide (1.44 g, 36 m mol) in methanol (8 ml). A slight exotherm was noted and stirring was continued for 16 hrs. The mixture was filtered and the collected solid washed several times with water and once with cold methanol to yield a yellow powder (1.60 g) with mp. 137° C. (lit. mp. 137°-138° C., see J. Heterocyclic Chem. 11, 107 (1974)).

Workup

  1. filtrationThe mixture was filtered
  2. washthe collected solid washed several times with water

Sources & evidence

ORD record
ord-b4fca40d17e94cf8a981e4aef9df9372
Source dataset
uspto-grants-1986_04
Patent number
US04579679

Reaction notes

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