Hydrochloric Acid → HCID 69560923, compound

HRID 1794339Notes

Reaction equation

HRID 1794339 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][OH:15])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 69561185HCID 69561185, compound

Product 1

HCID 69560923HCID 69560923, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-methylthiophenyl)isoxazole-4-carboxylate (10.0 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (0.95 M hexane solution, 92 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained crystals were recrystallized from ethyl acetate-isopropyl ether to give 5-(4-methylthiophenyl)-4-isoxazolylmethanol (7.50 g, yield 89%) as a colorless prism. melting point: 102–103° C.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe obtained crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-93c3208f8cf045ff939138bc1e10c0c5
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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