Methanol → HCID 18953970, compound

HRID 1491671Notes

Reaction equation

HRID 1491671 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][C:14](OCC)=[O:15])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CO>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][OH:15])[O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 15232754HCID 15232754, compound

Product 1

HCID 18953970HCID 18953970, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-phenyl-2-oxazolepropionate (1.4 g) in THF (20 ml) was added sodium borohydride (0.86 g). Methanol (4 ml) was dropwise added to the mixture over a period of 10 minutes under reflux. The reaction mixture was refluxed for further 30 minutes, concentrated, made acidic and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4 and distilled to obtain crystals of 3-(4-phenyl-2-oxazolyl)propanol (1.07 g, 92%). Recrystallization from ether-hexane gave colorless prism crystals of mp 55°-56° C.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was refluxed for further 30 minutes
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over MgSO4
  7. distillationdistilled

Sources & evidence

ORD record
ord-fef3ff11db004fdbb06ce3ea9dba2177
Source dataset
uspto-grants-1994_12
Patent number
US05371098

Reaction notes

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