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Sodium hydride → 2-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-2-phenyloxirane

HRID 349717
Notes
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Reaction equation

HRID 349717 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:33])([F:32])[C:11]1[CH:12]=[C:13]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:14][O:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>CS(C)=O.C(OCC)(=O)C>[F:9][C:10]([F:32])([F:33])[C:11]1[CH:12]=[C:13]([CH:25]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:27]=1)[CH2:14][O:15][CH2:16][C:17]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:2][O:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 229606442-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenylethan-1-one

Product 1

HCID 860918462-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-2-phenyloxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

Trimethylsulfoxonium iodide (185 mg, 0.84 mmol) was dissolved in anhydrous dimethylsulfoxide (2 ml). Sodium hydride (60 wt % in mineral oil, 36 mg, 0.9 mmol) was added to the solution and followed by addition of (2-(3,5-bis(trifluoromethyl)benzyloxy)-1-phenylethanone). After stirred for 1 hour, the reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate, concentrated, and the residue was purified by flash chromatography on silica gel to give the desired product. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 7.76 (s, 1 H) 7.69 (s, 2 H) 7.40–7.45 (m, 2 H) 7.34–7.39 (m, 2 H) 7.30–7.34 (m, 1 H) 4.65–4.72 (m, 2 H) 4.23 (d, J=11.90 Hz, 1 H) 3.79 (d, J=11.60 Hz, 1 H) 3.11 (d, J=5.19 Hz, 1 H) 2.82 (d, J=5.19 Hz, 1 H); LRMS [ESI, MNa+] m/z calcd for C18H14O2F6Na 399.08, found 398.97.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bf1c25f6d0bb47d6913da289e20044bc
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179926B2

Reaction notes

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