Thionyl Chloride → 4-(4-Chloromethylphenoxymethyl)-2-phenyloxazole

HRID 350001Notes

Reaction equation

HRID 350001 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([O:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][CH:9]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 230248884-(2-Phenyl-4-oxazolylmethoxy)benzylalcohol

Product 1

HCID 230219114-(4-Chloromethylphenoxymethyl)-2-phenyloxazoleYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(2-phenyl-4-oxazolylmethoxy)benzylalcohol (2.39 g), thionyl chloride (0.69 ml) and toluene (50 ml) was stirred at 40° C. overnight, and then the reaction mixture was concentrated. Saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 4-(4-chloromethylphenoxymethyl)-2-phenyloxazole (2.34 g, yield 92%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 129–130° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionSaturated aqueous sodium bicarbonate solution was added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9abec36680de4f429eaeb59eb66aac19
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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