Dimethyl Carbonate → HCID 68630388, compound

HRID 1855400Notes

Reaction equation

HRID 1855400 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14](=[O:16])[CH3:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[C:17](=O)([O:20]C)[O:18][CH3:19].S([O-])(O)(=O)=O.[Na+]>O1CCOCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:14](=[O:16])[CH2:15][C:17]([O:18][CH3:19])=[O:20])[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 212584081-[1-(4-Chlorophenyl)cyclobutyl]ethanone

Product 1

HCID 68630388HCID 68630388, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (1.86 g of a 60% dispersion in mineral oil, 46.5 mmol) was added to a solution of 1-[1-(4-chlorophenyl)cyclobutyl]ethanone (4.18 g, 20.0 mmol) and of dimethyl carbonate (8.4 mL, 99.6 mmol) in of dioxane (20 mL). After the reaction mixture had been refluxed for 4 h, it was chilled in an ice-water bath and treated drop wise with 1 M aqueous sodium hydrogen sulfate solution (50 mL). The mixture containing now a thick precipitate was then partitioned between diethyl ether and water. The organic phase was washed with sat. sodium hydrogen carbonate solution and with brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using heptane/0-10% ethyl acetate as eluent to afford the title compound (4.45 g, 79%) as pale-yellow oil.

Workup

  1. temperatureAfter the reaction mixture had been refluxed for 4 h
  2. temperatureit was chilled in an ice-water bath
  3. additionThe mixture containing now a thick precipitate
  4. customwas then partitioned between diethyl ether and water
  5. washThe organic phase was washed with sat. sodium hydrogen carbonate solution and with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-05d8c2c15103488eb272ca3cf902bfce
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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