Hydrochloric Acid → HCID 22221245, compound

HRID 1794386Notes

Reaction equation

HRID 1794386 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][C:14](OC)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][CH2:14][OH:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221437HCID 22221437, compound

Product 1

HCID 22221245HCID 22221245, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(5-phenyl-4-isoxazolyl)propionate (18.13 g) in tetrahydrofuran (300 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 160 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 residue was subjected to silica gel column chromatography, and 3-(5-phenyl-4-isoxazolyl)propan-1-ol (15.72 g, yield 99%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). NMR (CDCl3) δ: 1.82–2.00 (2H, m), 2.72–2.88 (2H, m), 3.66–3.78 (2H, m), 7.41–7.56 (3H, m), 7.68–7.78 (2H, m), 8.21 (1H, s).

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

Sources & evidence

ORD record
ord-2fa03232a500445ab9304f76d3ef43db
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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