Water → 5-[4-(Sec-butyloxy)-phenoxymethyl]-3-cyclopropyl-1,2,4-oxadiazole

HRID 1742833Notes

Reaction equation

[CH:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH2:3][CH3:4])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[O:25][N:24]=[C:23]([CH:26]2[CH2:28][CH2:27]2)[N:22]=1.O>CN(C)C=O>[CH:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:20][C:21]2[O:25][N:24]=[C:23]([CH:26]3[CH2:28][CH2:27]3)[N:22]=2)=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

5 g of 4-(sec-butyloxy)-phenol and 6.2 g of potassium carbonate are stirred in 50 ml of anhydrous dimethylformamide for 1 hour at 80° C. Subsequently, 4.8 g of 5-chloromethyl-3-cyclopropyl-1,2,4-oxadiazole in 20 ml anhydrous dimethylformamide is dripped in and the mixture stirred for 8 hours at 80° C. and overnight at room temperature (about 20° C.). The mixture is then poured into 100 ml of water and extracted three times with ethyl acetate, and the organic phases are dried over magnesium sulfate. The solvent is evaporated off and the crude product is purified by chromatography on silica gel using n-hexane/ethyl acetate (4:1) as eluant. There is obtained 6.7 g of 5-[4-(sec-butyloxy)-phenoxymethyl]-3-cyclopropyl-1,2,4-oxadiazole as a colorless oil.

Workup

extractionextracted three times with ethyl acetate
dry with materialthe organic phases are dried over magnesium sulfate
customThe solvent is evaporated off
customthe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-2e722019f3ff4dd3a065c63982dc8b53
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342849

Reaction notes

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