Hydrochloric Acid → HCID 22930681, compound

HRID 349970Notes

Reaction equation

HRID 349970 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][O:22][C:23]1[CH:27]=[C:26]([C:28](OC)=[O:29])[O:25][N:24]=1.Cl>O1CCCC1>[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[CH2:21][O:22][C:23]1[CH:27]=[C:26]([CH2:28][OH:29])[O:25][N:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22930703HCID 22930703, compound

Product 1

HCID 22930681HCID 22930681, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (1.0M tetrahydrofuran solution, 60 ml) was added slowly to a solution of methyl 3-(2-quinolylmethoxy)-5-isoxazolecarboxylate (7.39 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 saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated to obtain 3-(2-quinolylmethoxy)-5-isoxazolylmethanol (4.95 g, yield 74%) as colorless crystals. This was recrystallized from tetrahydrofuran-hexane. Melting point: 111–112° C.

Workup

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

Sources & evidence

ORD record
ord-15b63814d5824400a706946a5abedb0f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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