Ethyl 5-phenylisoxazole-3-carboxylate → (5-Phenyl-1,2-oxazol-3-yl)methanol

HRID 2248972Notes

Reaction equation

HRID 2248972 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:13][CH2:12][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:11][N:10]=1

Participants

4

Reactant 2

HCID 571142Ethyl 5-phenylisoxazole-3-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 1481082(5-Phenyl-1,2-oxazol-3-yl)methanolYield 44.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 5-phenylisoxazole-3-carboxylate (5.90 g, 27 mmol) in ether (30 ml) was added dropwise to a suspension of lithium aluminium hydride in ether (20 ml). When addition was complete, the mixture was heated at reflux for 1 h then a further quantity of lithium aluminium hydride (0.25 g) was added and reflux continued for 0.5 h. The reaction was cautiously quenched with 2% sulphuric acid and the ether layer separated, dried (MgSO4) and the solvent removed under reduced pressure to yield 3-hydroxymethyl-5-phenylisoxazole (2.10 g, 12 mmol, 44%); δH (CDCl3) 3.60(1H,br,OH), 4.75(2H,s,CH2), 6.35(1H,s,CH), 7.2-7.8(5H,m,C6H5).

Workup

  1. additionWhen addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 1 h
  4. temperaturereflux
  5. customThe reaction was cautiously quenched with 2% sulphuric acid
  6. customthe ether layer separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-593911932bd34cd894c735032a615753
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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