Benzyl Alcohol → 3-(Benzyloxy)-4-(2-methyl-1,3-oxazol-5-yl)benzonitrile

HRID 71198Notes

Reaction equation

HRID 71198 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[C:20]1[O:24][C:23]([CH3:25])=[N:22][CH:21]=1)[C:15]#[N:16]>CN(C=O)C.O>[CH2:3]([O:10][C:18]1[CH:17]=[C:14]([CH:13]=[CH:12][C:19]=1[C:20]1[O:24][C:23]([CH3:25])=[N:22][CH:21]=1)[C:15]#[N:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 66607929HCID 66607929, compound

Product 1

HCID 666076073-(Benzyloxy)-4-(2-methyl-1,3-oxazol-5-yl)benzonitrileYield 103.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of sodium hydride (60%, 2.1 g) in DMF (35 mL) was added benzylalcohol (5.61 g) at 0° C., and the mixture was stirred for 30 min. 3-Fluoro-4-(2-methyl-1,3-oxazol-5-yl)benzonitrile (3.50 g) was added to this reaction mixture at 0° C., and the mixture was stirred at room temperature for 1 hr, and diluted with water. The resultant precipitate was collected by filtration and washed with water to give the title compound (5.20 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-fd968faf35374cc187596199041662f1
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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