Water → 2-[(4-Chlorophenoxy)-methyl]-2-(1-ethoxycarbonyl-cycloprop-1-yl)-oxirane

HRID 704521Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12]([C:14]1([C:17]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:18])[CH2:16][CH2:15]1)=[O:13])[CH3:10].O>CS(C)=O>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:17]2([C:14]3([C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:15][CH2:16]3)[CH2:4][O:18]2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 20 °C

Procedure

3.6 g (0.13 mol) of 80% strength sodium hydride are added under an argon atmosphere and with stirring at 10° to 20° C. to a suspension of 24 g (0.11 mol) of trimethylsulphoxonium iodide in 100 ml of dimethyl sulphoxide. After stirring for 30 minutes at 20° C., 17.1 g (0.061 mol) of 4-chlorophenoxymethyl 1-ethoxycarbonylcycloprop-1-yl ketone are added. The mixture is warmed to 60° C. for 1 hour. After this, the mixture is poured into 300 ml of water and extracted with methylene chloride. The combined organic extracts are washed with water, dried over magnesium sulphate and concentrated. 14 g (77.8% of theory) of 2-[(4-chlorophenoxy)-methyl]-2-(1-ethoxycarbonyl-cycloprop-1-yl)-oxirane are obtained as an oil which is further reacted without additional purification. ##STR18##

Workup

temperatureThe mixture is warmed to 60° C. for 1 hour
extractionextracted with methylene chloride
washThe combined organic extracts are washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-8b37f31efbce4f0cbea5d6b55a27dc20
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988383

Reaction notes

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