Potassium Carbonate → 5-Methyl-2-[(4-phenoxyphenoxy)-methyl]-1,3,4-oxadiazole

HRID 2166102Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]1[O:24][C:25]([CH3:28])=[N:26][N:27]=1>CN(C)C=O>[CH3:28][C:25]1[O:24][C:23]([CH2:22][O:14][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)=[N:27][N:26]=1

Participants

Conditions

Temperature: 20 °C

Procedure

9.3 g of 4-phenoxyphenol and 9 g of potassium carbonate are stirred in 75 ml of anhydrous dimethylformamide for 1 hour at 80° C. Subsequently, 6.6 g of 2-chloromethyl-5-methyl-1,3,4-oxadiazole in 20 ml of anhydrous dimethylformamide is dripped in. The mixture is stirred for 10 hours at 80° C. and at room temperature (approx. 20° C.) overnight. The mixture is then stirred into 500 ml of ice water and extracted three times with ethyl acetate. After drying over sodium sulfate and removal of the solvent, the residue is purified by chromatography over silica gel using n-hexane/ethyl acetate (4:1) as eluant. There is obtained 12 g of 5-methyl-2-[(4-phenoxyphenoxy)-methyl]-1,3,4-oxadiazole; colorless crystals; m.p.: 78°-79° C.

Workup

extractionextracted three times with ethyl acetate
dry with materialAfter drying over sodium sulfate and removal of the solvent
customthe residue is purified by chromatography over silica gel

Sources & evidence

ORD record: ord-e6e61de5f8af40968739313c0390f17a
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04943584

Reaction notes

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