Sodium hydride → HCID 57809804, compound

HRID 2106022Notes

Reaction equation

HRID 2106022 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:17])([CH3:16])[CH2:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1.[I-].[CH3:19][S+](C)(C)=O.[H-].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:17])([CH3:16])[CH2:9][C:10]2([C:11]([F:13])([F:14])[F:12])[CH2:19][O:15]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)2×HCID 57810019HCID 57810019, compound

Product 1

HCID 57809804HCID 57809804, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of 4-(3-bromophenyl)-1,1,1-trifluoro-4-methylpentan-2-one (68 mg, 2.2 mmol) in 2.9 mL of anhydrous DMSO was added over 5 minutes a solution the ylide of trimethylsulfoxonium iodide (3.3 mL of a 0.8M DMSO solution prepared from 2.66 g (12.1 mmol) of trimethylsulfoxonium iodide in 15 mL of anhydrous DMSO and 483 mg of 60% NaH in mineral oil (12.1 mmol) added in portions and aged for 30 minutes). The mixture stirred 2 hours and quenched with water and ethyl acetate. The organic phase was washed with water and brine, and dried over sodium sulfate. Removal of the volatiles in vacuo afforded the yellow oil 2-[2-(3-bromophenyl)-2-methylpropyl]-2-trifluoromethyloxirane which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-6a8a1ab0ea9048adaf794536afb5ea87
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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