Thionyl Chloride → 4-Chloromethyl-2-phenyl-5-propyloxazole

HRID 1294162Notes

Reaction equation

HRID 1294162 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH2:14][CH2:15][CH3:16])=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][C:9]=1[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178612102-Phenyl-5-propyl-4-oxazolylmethanol

Product 1

HCID 178613954-Chloromethyl-2-phenyl-5-propyloxazoleYield 151%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-phenyl-5-propyl-4-oxazolylmethanol (1.38 g) and toluene (100 mL) was added thionyl chloride (1.38 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 4-chloromethyl-2-phenyl-5-propyloxazole as a colorless oil (2.26 g, 99%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45e9cf638f1847c484d57469216781e0
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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