Hydrochloric Acid → HCID 22221203, compound

HRID 1794397Notes

Reaction equation

HRID 1794397 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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 22221082HCID 22221082, compound

Product 1

HCID 22221203HCID 22221203, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(2,4-difluorophenyl)-4-isoxazolyl]propionate (1.05 g) in tetrahydrofuran (30 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 8.7 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-(2,4-difluorophenyl)-4-isoxazolyl]propan-1-ol (640 mg, yield 68%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR (CDCl3) δ: 1.29 (1H, br s), 1.75–1.95 (2H, m), 2.55–2.65 (2H, m), 3.6–3.75 (2H, m), 6.9–7.1 (2H, m), 7.5–7.65 (1H, m), 8.25 (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-9052a72f267445188ed4789622ba0885
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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