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

HRID 349958Notes

Reaction equation

HRID 349958 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][O:24][C:25]1[CH:29]=[C:28]([C:30](OC)=[O:31])[O:27][N:26]=1.Cl>O1CCCC1>[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:14][C:13]=1[CH2:23][O:24][C:25]1[CH:29]=[C:28]([CH2:30][OH:31])[O:27][N:26]=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

Diisobutylaluminium hydride (1.0M tetrahydrofuran solution, 60 ml) was added slowly to a solution of methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isooxazolecarboxylate (7.86 g) in tetrahydrofuran (150 ml) at 0° C., which was stirred at room temperature for 30 minutes. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated to obtain 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (5.93 g, yield 86%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 99–100° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-46b27fd88ae84c5e82008bb004b2e4d2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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