Water → 3-(Chloromethyl)-5-phenyl-1,2-oxazole

HRID 584382Notes

Reaction equation

HRID 584382 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]2[O:15][N:14]=[C:13]([CH2:16]O)[CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>C1(C)C=CC=CC=1>[Cl:3][CH2:16][C:13]1[CH:12]=[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:15][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 1481082(5-Phenyl-1,2-oxazol-3-yl)methanol

Product 1

HCID 14847693-(Chloromethyl)-5-phenyl-1,2-oxazoleYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (7.55 ml) was added to a solution of (5-phenyl-3-isoxazolyl)methanol (12.1 g) in toluene (50 ml) and stirred at 80° C. for 3 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 3-(chloromethyl)-5-phenylisoxazole (11.8 g, yield 88%) as pale-yellow crystals. m.p. 46-47° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8e496d887a9e480584154f7d4967fd30
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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