Thionyl Chloride → 5-Chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole

HRID 1294155Notes

Reaction equation

HRID 1294155 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20]O)[O:17][N:16]=1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:24][CH2:20][C:18]1[O:17][N:16]=[C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])[CH:19]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178612053-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol

Product 1

HCID 178612855-Chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazoleYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (2.86 g) in toluene (50 ml) was slowly added thionyl chloride (0.80 mL) at room temperature and the mixture was stirred under reflux for 30 min. After cooling, the reaction mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 5-chloromethyl-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)isoxazole (2.70 g, yield 89%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 105-106° C.

Workup

  1. customat room temperature
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4658ae750ce146b4ac34436421351ff9
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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