Cesium acetate → Acetic Acid 2-phenylbenzoxazol-5-ylmethyl Ester

HRID 970816

Reaction equation

HRID 970816 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:17]=1.[C:18]([O-:21])(=[O:20])[CH3:19].[Cs+]>CN(C=O)C>[C:11]1([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][O:21][C:18](=[O:20])[CH3:19])=[CH:17][C:7]=3[N:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5152919Cesium acetateHCID 220628305-Bromomethyl-2-phenylbenzoxazole

Product 1

HCID 23581212Acetic Acid 2-phenylbenzoxazol-5-ylmethyl EsterYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromomethyl-2-phenylbenzoxazole 56 (1.0 g, 3.4 mmol) and cesium acetate (1.33 g, 6.94 mmol) were stirred together in DMF(25 ml) under an atmosphere of N2 overnight. The DMF was evaporated under high vacuum and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The ethyl acetate layer was separated then washed and dried. Evaporation of the solvent yielded 920 mg of acetic acid 2-phenylbenzoxazol-5-ylmethyl ester 57.

Workup

  1. customThe DMF was evaporated under high vacuum
  2. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. customThe ethyl acetate layer was separated
  4. washthen washed
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-31328c837bef439eb38fa3f8aab89051
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Linked notes

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