Hydrochloric Acid → HCID 22221156, compound

HRID 1794435Notes

Reaction equation

HRID 1794435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:11][O:10][N:9]=2)=[CH:4][C:3]=1[F:19].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:11][O:10][N:9]=2)=[CH:4][C:3]=1[F:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221275HCID 22221275, compound

Product 1

HCID 22221156HCID 22221156, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[3-(4-chloro-3-fluorophenyl)-4-isoxazolyl]propionate (3.69 g) in tetrahydrofuran (30 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-(4-chloro-3-fluorophenyl)-4-isoxazolyl]propan-1-ol (3.06 g, yield 92%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 54–55° C.

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-6a9e8ac80e294337943e3673d826127c
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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