3-Methoxyacetophenone → 2-(3-Methoxyphenyl)-2-methyloxirane

HRID 2198882Notes

Reaction equation

HRID 2198882 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[O:11].O1CCC[CH2:21]1.CS(C)=O>CS(C)=O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:10]2([CH3:21])[CH2:9][O:11]2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 114603-MethoxyacetophenoneHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 21830753dimethylsulfoxide THF

Product 1

HCID 204969162-(3-Methoxyphenyl)-2-methyloxirane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Trimethyloxosulphonium iodide (100 g, 0.45 mole) was added as a slurry in dimethylsulphoxide (100 ml) to a stirred cooled suspension of sodium hydride (22.6 g of a 50% dispersion of oil, washed free from oil with ether) under nitrogen, keeping the internal temperature at 20° C. by ice-cooling. After stirring at room temperature for 1 hour 3-methoxyacetophenone (45 g, 0.3 mole) was added in a 1:1 mixtures of dry tetrahydrofuran-dimethylsulphoxide (100 ml). The reaction mixture was slowly heated to 50° C. over 1 hour and this temperature was maintained for 1 hour. The mixture was cooled, poured on to ice water and extracted with ether (4×150 ml). The combined extracts were washed with brine, dried (MgSO4) and evaporated to an oil (34.0 g) and used crude for the preparation of (3-methoxy)-α-methyl-α[(methylamino)methyl]benzene methanol.

Workup

  1. temperaturecooled
  2. washwashed free from oil with ether) under nitrogen
  3. customat 20° C.
  4. temperaturecooling
  5. temperaturethis temperature was maintained for 1 hour
  6. temperatureThe mixture was cooled
  7. extractionextracted with ether (4×150 ml)
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated to an oil (34.0 g)
  11. customfor the preparation of (3-methoxy)-α-methyl-α[(methylamino)methyl]benzene methanol

Sources & evidence

ORD record
ord-593dcb76c2594f9db37f4c7078e30a68
Source dataset
uspto-grants-1982_11
Patent number
US04360519

Reaction notes

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