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Sodium hydride → 5-{7-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran-5-yl}pyrimidine

HRID 400656
Notes
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Reaction equation

HRID 400656 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3](=[O:23])[CH2:4][C:5]([CH3:22])([C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[N:20][CH:21]=2)[CH:8]=1)[CH3:6].[CH3:26][S+](C)(C)=O.[H-].[Na+].[I-].C[S+](C)(C)=O>CS(C)=O.C1COCC1.CS(C)=O.O>[CH3:6][C:5]([C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([C:16]2[CH:21]=[N:20][CH:19]=[N:18][CH:17]=2)[CH:8]=1)([CH3:22])[CH2:4][C:3]1([C:2]([F:24])([F:1])[F:25])[CH2:26][O:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 74499TrimethylsulfoxoniumHCID 600265371,1,1-Trifluoro-4-methyl-4-(5-pyrimidin-5-yl-2,3-dihydrobenzofuran-7-yl)pentan-2-one

Product 1

HCID 600262855-{7-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran-5-yl}pyrimidineYield 99%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 21830753dimethylsulfoxide THFSolvent

Procedure

To a solution of 1,1,1-trifluoro-4-methyl-4-(5-pyrimidin-5-yl-2,3-dihydrobenzofuran-7-yl)pentan-2-one (620 mg, 1.8 mmol) in 5 mL of anhydrous DMSO-THF (1:1) was added 2.64 mL of a trimethylsulfoxonium ylide solution (stock solution prepared by reaction of NaH (242 mg, 60% dispersion in mineral oil) with trimethylsulfoxonium iodide (1.33 g, 6.0 mmol) in 7.50 mL of anhydrous DMSO for 30 minutes) dropwise over 5 minutes. After stirring for 2 hour at room temperature, the reaction mixture was poured into 40 mL of water and extracted with diethyl ether (200 mL total volume). The combined organic phases were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 651 mg (99% yield) of the title compound as a pale yellow oil which was used without further purification.

Workup

  1. extractionextracted with diethyl ether (200 mL total volume)
  2. washThe combined organic phases were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cb6a45988d6443d80abc87aea48340c
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741897B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes