Sulfoxonium, trimethyl-, iodide (1:1) → HCID 57810032, compound

HRID 2106031Notes

Reaction equation

HRID 2106031 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3](=[O:20])[CH2:4][C:5]([CH3:19])([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2([CH3:18])[O:17][CH2:16][CH2:15][O:14]2)[CH:8]=1)[CH3:6].[Na].[I-].[CH3:25][S+](C)(C)=O>CS(C)=O>[CH3:19][C:5]([C:7]1[CH:8]=[C:9]([C:13]2([CH3:18])[O:14][CH2:15][CH2:16][O:17]2)[CH:10]=[CH:11][CH:12]=1)([CH3:6])[CH2:4][C:3]1([C:2]([F:1])([F:21])[F:22])[CH2:25][O:20]1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5360545SodiumHCID 578100111,1,1-Trifluoro-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]pentan-2-one

Product 1

HCID 57810032HCID 57810032, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 1,1,1-trifluoro-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]pentan-2-one (0.56 g, 1.8 mmol) in anhydrous DMSO (2.3 mL) was added the sodium ylide of trimethylsulfoxonium iodide (2.6 mL of a 0.8M solution in DMSO) over 5 minutes. The mixture was stirred 2 hours, quenched with water, and extracted with ethyl acetate. The combined organic layers were washed with water and brine, and dried over sodium sulfate. The solution was concentrated in vacuo to afford the yellow oil, 2-{3-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-2-methyl-[1,3]dioxolane, which was used without further purification.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-688ad17e84554d9385870f5ea7bbfb57
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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