Tetrahydrofuran → 430535-13-0

HRID 1794332Notes

Reaction equation

HRID 1794332 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12]O)=[CH:4][CH:3]=1.O1CCCC1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH2:12][C:8]1[CH:9]=[N:10][O:11][C:7]=1[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 22221030HCID 22221030, compound

Product 1

HCID 22221332430535-13-0Yield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 5-(5-chloro-2-thienyl)-4-isoxazolylmethanol (6.54 g), tetrahydrofuran (20 ml) and toluene (100 ml) was added dropwise thionyl chloride (5.41 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 residue was subjected to silica gel column chromatography, and crystals of 4-chloromethyl-5-(5-chloro-2-thienyl)isoxazole (6.98 g, yield 98%) were obtained from a fraction eluted with ethyl acetate-hexane (1:5, volume ratio) and recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 70–71° 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

Sources & evidence

ORD record
ord-6994acdbd83745d39055188979b8b893
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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