Dimethyl Sulfide → HCID 14700143, compound

HRID 704520Notes

Reaction equation

S([O:6][CH3:7])(OC)(=O)=O.CSC.C[O-].[Na+].[Cl:14][C:15]1[CH:35]=[CH:34][C:18]([CH2:19][C:20]2([C:23]([CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=O)[CH2:22][CH2:21]2)=[CH:17][CH:16]=1>C(#N)C.O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][C:23]2([C:20]3([CH2:19][C:18]4[CH:17]=[CH:16][C:15]([Cl:14])=[CH:35][CH:34]=4)[CH2:22][CH2:21]3)[CH2:7][O:6]2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 20 °C

Procedure

21 g (0.17 mol) of dimethyl sulphate are added dropwise with stirring at 20° C. to a solution of 10.5 g (0.17 mol) of dimethyl sulphide in 100 ml of acetonitrile. After standing for 2 days at 20° C., 9.2 g (0.17 mol) of sodium methoxide is added to this solution, the mixture is stirred for 30 minutes at 20° C. and then 29 g (0.09 mol) of 4-chlorophenoxymethyl 1-(4-chlorobenzyl)cycloprop-1-yl ketone are added. After stirring for 16 hours at 20° C., the reaction mixture is poured into water and the mixture is extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and concentrated under reduced pressure. 25.2 g (80% of theory) of 2-(4-chlorophenoxymethyl)-2-[(4-chlorobenzyl)cycloprop-1-yl]-oxirane are obtained in the form of a colorless oil which is employed for further synthesis without additional purification. ##STR14##

Workup

stirringAfter stirring for 16 hours at 20° C.
extractionthe mixture is extracted with methylene chloride
washThe organic phase is washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2289cffa67684c8cbffc6fd925982417
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988383

Reaction notes

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