Hydrochloric Acid → (5-Phenyl-1,2-oxazol-3-yl)methanol

HRID 2299738Notes

Reaction equation

HRID 2299738 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-].O.Cl>C(OCC)C.C(OCC)(=O)C>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 571142Ethyl 5-phenylisoxazole-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1481082(5-Phenyl-1,2-oxazol-3-yl)methanolYield 94.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 5-phenylisoxazole-3-carboxylate (20.0 g) in diethyl ether (50 ml) was added dropwise to a mixture of lithium aluminium hydride (2.62 g) in diethyl ether (50 ml) at 0° C. After stirring for 1 hour, water was added to the reaction mixture carefully, followed by addition of 1N hydrochloric acid (200 ml) and extraction with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain (5-phenyl-3-isoxazolyl)methanol (15.2 g, yield 94%) as pale-brown crystals. m.p. 101-102° C.

Workup

  1. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-de8f30b4d372410899578406a8f0ff10
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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