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

HRID 584380Notes

Reaction equation

HRID 584380 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-18650a4430db4f74b07432c218d0b298
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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