2-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl ester → (5-Phenyl-4,5-dihydro-1,2-oxazol-3-yl)methanol

HRID 434517Notes

Reaction equation

HRID 434517 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12](OCC)=[O:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[OH:13][CH2:12][C:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:11][N:10]=1

Participants

4

Reactant 2

HCID 5388222-Isoxazoline-3-carboxylic acid, 5-phenyl-, ethyl esterHCID 4311764Sodium borohydride

Product 1

HCID 12794210(5-Phenyl-4,5-dihydro-1,2-oxazol-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7 g of ethyl 5-phenyl-4,5-dihydroisoxazol-3-ylcarboxylate in 70 ml of methanol, cooled with ice, is added 1.5 g of sodium borohydride in small portions with stirring. After 4 hours has passed, the solvent is distilled off under reduced pressure and the residue is extracted with ethyl acetate. The extract is washed with water, dried and the solvent is evaporated. The crystalline residue thus obtained is recrystallized from isopropyl ether, giving 3-hydroxymethyl-5-phenyl-4,5-dihydroisoxazole in the form of white crystals. Melting point: 73°-74° C.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customthe solvent is evaporated
  6. customThe crystalline residue thus obtained
  7. customis recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-2c30780d8f2c4680a413e63e96597abd
Source dataset
uspto-grants-1983_08
Patent number
US04397853

Reaction notes

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