Tetrahydrofuran → 4-Chloromethyl-5-(4-trifluoromethylphenyl)isoxazole

HRID 1794327Notes

Reaction equation

HRID 1794327 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14]O)=[CH:5][CH:4]=1.O1CCCC1.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][CH2:14][C:10]1[CH:11]=[N:12][O:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 222214255-(4-Trifluoromethylphenyl)-4-isoxazolylmethanol

Product 1

HCID 222211934-Chloromethyl-5-(4-trifluoromethylphenyl)isoxazoleYield 77.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 5-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (5.65 g), tetrahydrofuran (20 ml) and toluene (80 ml) was added dropwise thionyl chloride (4.15 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, saturated aqueous sodium hydrogencarbonate was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated and recrystallized from ethyl acetate-hexane to give 4-chloromethyl-5-(4-trifluoromethylphenyl)isoxazole (4.70 g, yield 77%) as a colorless prism. melting point: 99–100° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogencarbonate was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. filtrationThe obtained colorless crystals were filtrated
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dbc12715e25745b9986b950177d78cbb
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…