Hydrochloric Acid → 3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol

HRID 1294154Notes

Reaction equation

HRID 1294154 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([C:20](OC)=[O:21])[O:17][N:16]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17861331Methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178612053-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylate (7.86 g) in tetrahydrofuran (150 mL) was slowly added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 60 mL) at 0° C. and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (5.93 g, yield 86%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 99-100° C.

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e34723ef91b43dda556290fe39eae3c
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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