Thionyl Chloride → 3-(Chloromethyl)-5-phenyl-4,5-dihydro-1,2-oxazole

HRID 434518Notes

Reaction equation

HRID 434518 reaction equation
O[CH2:2][C:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.S(Cl)([Cl:16])=O>CCOCC>[Cl:16][CH2:2][C:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12794210(5-Phenyl-4,5-dihydro-1,2-oxazol-3-yl)methanol

Product 1

HCID 114582493-(Chloromethyl)-5-phenyl-4,5-dihydro-1,2-oxazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Hydroxymethyl-5-phenyl-4,5-dihydroisoxazole (3.2 g) is dissolved in 50 ml of anhydrous ether. To the solution cooled with ice is slowly added dropwise 2.6 g of thionyl chloride with stirring. The reaction mixture is allowed to stand overnight at room temperature and then the solvent is distilled off to give 3-chloromethyl-5-phenyl-4,5-dihydroisoxazole in the form of yellow brown oil.

Workup

  1. temperatureTo the solution cooled with ice
  2. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-1dc2175c4dd2413eb94467fd47add291
Source dataset
uspto-grants-1983_08
Patent number
US04397853

Reaction notes

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