Thionyl Chloride → HCID 22221311, compound

HRID 1794321Notes

Reaction equation

HRID 1794321 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:17]([CH2:18]O)=[CH:16][O:15][N:14]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>>[Cl:22][CH2:18][C:17]1[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)=[N:14][O:15][CH:16]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22221040HCID 22221040, compound

Product 1

HCID 22221311HCID 22221311, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(4-phenylphenyl)-4-isoxazolylmethanol (4.16 g) and thionyl chloride (10.0 ml) was stirred at 0° C. for 30 min. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate was added to the residue. The mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated to give 4-chloromethyl-3-(4-phenylphenyl)isoxazole (3.84 g, yield 92%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 102–103° 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

Sources & evidence

ORD record
ord-ac7d6558fd584483b738b97314bc88a3
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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