Hydrochloric Acid → HCID 22220983, compound

HRID 1794459Notes

Reaction equation

HRID 1794459 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14][CH2:15][C:16](OC)=[O:17].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221215HCID 22221215, compound

Product 1

HCID 22220983HCID 22220983, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(2,5-dichlorophenyl)-4-isoxazolyl]propionate (500 mg) in tetrahydrofuran (30 ml) was gently added diisobutylaluminum hydride (1.0 M toluene solution, 4.2 ml) 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-(2,5-dichlorophenyl)-4-isoxazolyl]propan-1-ol (420 mg, yield 93%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR (CDCl3) δ: 1.28 (1H, t, J=5 Hz), 1.7–1.9 (2H, m), 2.5–2.6 (2H, m), 3.65 (2H, td, J=6, 5 Hz), 7.35–7.5 (3H, m), 8.27 (1H, s).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abed9e327acd48c5b4c316069aa9ff2d
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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