Tetrahydrofuran → HCID 54174730, compound

HRID 2371914Notes

Reaction equation

HRID 2371914 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].O1CCC[CH2:10]1.[Cl:14][CH:15]([F:34])[C:16]([F:33])([F:32])[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([C:28]2([Cl:31])[CH2:30][CH2:29]2)=[O:27])=[CH:20][CH:19]=1>CS(C)=O>[Cl:31][C:28]1([C:26]2([CH:25]=[CH:24][C:21]3[CH:22]=[CH:23][C:18]([O:17][C:16]([F:32])([F:33])[CH:15]([Cl:14])[F:34])=[CH:19][CH:20]=3)[CH2:10][O:27]2)[CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 53914210HCID 53914210, compound

Product 1

HCID 54174730HCID 54174730, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 6.35 g (0.031 mole) of trimethylsulphoxonium iodide in 20 ml of dimethyl sulphoxide is added at -15° C. with stirring to a suspension of 0.75 g (0.031 mole) of sodium hydride in 25 ml of a mixture of dimethyl sulphoxide: tetrahydrofuran=3:2. After warming the reaction mixture to 0° C., a solution of 9.6 g (0.028 mole) of 1-chloro-cyclopropyl 4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl-ethenyl ketone in 15 ml of dimethyl sulphoxide is added dropwise with stirring. The mixture is subsequently stirred at 0° C. for 15 minutes and at room temperature for 45 minutes. The reaction mixture is then poured into 100 ml of ice water and the mixture is extracted three times with cyclohexane. The combined organic phases are washed once with water, dried over sodium sulphate and then concentrated under reduced pressure. 8.89 g (89% of theory) of 2-(1-chloro-cyclo-propyl)-2-[4-(2 -chloro-1,1,2-trifluoroethoxy)-phenylethenyl]-oxirane are obtained in this way in the form of an oily product which is reacted further without additional purification. ##STR38##

Workup

  1. stirringThe mixture is subsequently stirred at 0° C. for 15 minutes and at room temperature for 45 minutes
  2. extractionthe mixture is extracted three times with cyclohexane
  3. washThe combined organic phases are washed once with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e20e181c954e4f099f7a697c99ca65b7
Source dataset
uspto-grants-1992_03
Patent number
US05096912

Reaction notes

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