Hydrochloric Acid → HCID 22220987, compound

HRID 1794433Notes

Reaction equation

HRID 1794433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([CH2:14][CH2:15][C:16](OC)=[O:17])=[CH:12][O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:12][O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221219HCID 22221219, compound

Product 1

HCID 22220987HCID 22220987, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[3-(3-chloro-4-fluorophenyl)-4-isoxazolyl]propionate (3.50 g) in tetrahydrofuran (50 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 30 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-[3-(3-chloro-4-fluorophenyl)-4-isoxazolyl]propan-1-ol (2.89 g, yield 92%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). NMR (CDCl3) δ: 1.30 (1H, t, J=5.2 Hz), 1.74–1.94 (2H, m), 2.62–2.74 (2H, m), 3.64–3.76 (2H, m), 7.18–7.31 (1H, m), 7.50–7.60 (1H, m), 7.74 (1H, dd, J=2.2, 7.0 Hz), 8.29 (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-5c3aed8a40314b46b558bf15487f4d65
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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