Sulfoxonium, trimethyl-, iodide (1:1) → 2-{3-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-[1,3]dioxane

HRID 2106026Notes

Reaction equation

HRID 2106026 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([C:13]([CH3:22])([CH3:21])[CH2:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:10]=[CH:11][CH:12]=1.[Na].[I-].[CH3:25][S+](C)(C)=O>CS(C)=O>[CH3:21][C:13]([C:9]1[CH:8]=[C:7]([CH:2]2[O:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:12]=[CH:11][CH:10]=1)([CH3:22])[CH2:14][C:15]1([C:16]([F:18])([F:19])[F:17])[CH2:25][O:20]1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5360545SodiumHCID 578099664-(3-[1,3]Dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one

Product 1

HCID 578100032-{3-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-[1,3]dioxane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 4-(3-[1,3]dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one (1 g, 3 mmol) in 4.1 mL of anhydrous DMSO was added the sodium ylide of trimethylsulfoxonium iodide (3.0 mL of a 0.8M solution in DMSO) over 5 minutes. The reaction was stirred 2 hours and quenched with water and ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulfate. Removal of the volatiles in vacuo afforded 2-{3-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-[1,3]dioxane as a yellow oil.

Workup

  1. customquenched with water and ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-34c7cf95fdd44f9d88544189e1b1b972
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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