Water → HCID 19882460, compound

HRID 847160Notes

Reaction equation

HRID 847160 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11]1([C:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:15])[CH2:13][CH2:12]1.O>CS(C)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C:14]2([C:11]3([O:10][CH3:9])[CH2:13][CH2:12]3)[CH2:2][O:15]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 19882461HCID 19882461, compound

Product 1

HCID 19882460HCID 19882460, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

15 ml of absolute dimethyl sulphoxide are added dropwise at 10° C. under a nitrogen atmosphere to a mixture of 2.2 g (10 mmol) of trimehylsulphoxonium iodide and 0.4 g (13 mmol) of sodium hydride (80% pure). After addition is complete, the mixture is allowed to warm to room temperature in the course of 10 minutes and a solution of 2 g (9.6 mmol) of 4-fluorobenzyl 1-methoxycyclopropyl ketone in 10 ml of absolute dimethyl sulphoxide is then added dropwise with stirring. The reaction mixture is then poured into water. The resulting mixture is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. 1.5 g (70% of theory) of 2-(4-fluoro-benzyl)-2-(1-methoxy-cyclopropyl)-oxirane are obtained in this manner in the form of an oil. ##STR33##

Workup

  1. additionAfter addition
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85c6aa3102e34ae0a973cfb489f9fc63
Source dataset
uspto-grants-1992_08
Patent number
US05140035

Reaction notes

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