Thionyl Chloride → HCID 53776119, compound

HRID 1387366Notes

Reaction equation

HRID 1387366 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][N:7]=[C:8]([C:17]1[O:21][N:20]=[C:19]([CH3:22])[CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]O>C1C=CC=CC=1>[CH3:5][O:6][N:7]=[C:8]([C:17]1[O:21][N:20]=[C:19]([CH3:22])[CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][Cl:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53904665HCID 53904665, compound

Product 1

HCID 53776119HCID 53776119, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzene (5 ml) and thionyl chloride (0.36 g, 3.0 mmol) were added to 2-hydroxymethylphenyl 3-methylisoxazol-5-yl ketone O-methyloxime (0.62 g, 2.5 mmol), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-chloromethylphenyl 3-methylisoxazol-5-yl ketone O-methyloxime (0.26 g, yield: 39.3%) as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-ecc207f9d1f34f6b820e9861c6b1fc3e
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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