Water → HCID 57809818, compound

HRID 2106003Notes

Reaction equation

HRID 2106003 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:29])([F:28])[C:11](=[O:27])[CH2:12][C:13]([CH3:26])([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=1)[CH3:14].O>CS(C)=O>[CH3:26][C:13]([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=1)([CH3:14])[CH2:12][C:11]1([C:10]([F:9])([F:28])[F:29])[CH2:2][O:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 57809816HCID 57809816, compound

Product 1

HCID 57809818HCID 57809818, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of trimethylsulfoxonium iodide (1.36 g) in anhydrous dimethylsulfoxide (7.7 mL) was added sodium hydride (60% dispersion in mineral oil, 246 mg). The resulting solution was stirred at room temperature for 30 minutes and was then added dropwise to a solution of 1,1,1-trifluoro-4-methyl-4-(5-methylsulfanyl-2,3-dihydrobenzofuran-7-yl)pentan-2-one (1.63 g) in anhydrous dimethylsulfoxide (6.5 mL). After 2 hours, water (100 mL) was added and the resulting mixture was extracted with three 100 mL portions of diethyl ether. The combined organic phases were washed twice with water, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-5-methylsulfanyl-2,3-dihydrobenzofuran as a clear oil (1.64 g) which was used without further purification.

Workup

  1. waitAfter 2 hours
  2. extractionthe resulting mixture was extracted with three 100 mL portions of diethyl ether
  3. washThe combined organic phases were washed twice with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce733851ee0d4c8e931ec22ef798f0fc
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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