Hydrochloric Acid → HCID 22221421, compound

HRID 1794458Notes

Reaction equation

HRID 1794458 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15](OC)=[O:16])[S:5][C:6]=1[Cl:7].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][CH2:15][OH:16])[S:5][C:6]=1[Cl:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221290HCID 22221290, compound

Product 1

HCID 22221421HCID 22221421, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[5-(4,5-dichloro-2-thienyl)-4-isoxazolyl]propionate (1.30 g) in tetrahydrofuran (40 ml) was gently added diisobutylaluminum hydride (0.95 M hexane solution, 11.2 ml) at room temperature, and the mixture was stirred 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-(4,5-dichloro-2-thienyl)-4-isoxazolyl]propan-1-ol (1.05 g, yield 89%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR (CDCl3) δ: 1.35–1.5 (1H, m), 1.8–2.0 (2H, m), 2.65–2.8 (2H, m), 3.65–4.0 (2H, m), 7.29 (1H, s), 8.19 (1H, s).

Workup

  1. customat room temperature
  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-02842c1d02e7488483fee5c248fb36c7
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…