Methyl iodide → HCID 19367212, compound

HRID 324667Notes

Reaction equation

HRID 324667 reaction equation
CI.N12CCCN=C1CCCC[CH2:4]2.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]1[C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25](=[O:31])[CH2:24][CH2:23]1>CC(C)=O>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]1[C:27]([C:28]([O:30][CH3:4])=[O:29])=[CH:26][C:25](=[O:31])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22004691HCID 22004691, compound

Product 1

HCID 19367212HCID 19367212, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

235 g (1.66 mol) of methyl iodide and 212 g (1.39 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, dropwise, were successively added to a solution of 288 g (1.17 mol) of (RS)-6-(2-methoxyphenyl)-3-oxocyclohexene-1-carboxylic acid in 2.5 dm3 of acetone and then the mixture was brought to reflux for one hour. The acetone was subsequently concentrated and then the residue was stirred with 1 dm3 of water. After cooling to 10° C., the precipitate formed was filtered off, washed with petroleum ether and then dried at 50° C. 289 g (95%) of methyl (RS)-6-(2-methoxyphenyl)-3-oxocyclohexene-1-carboxylate were thus obtained in the form of a mustard-coloured powder, the characteristics of which were as follows:

Workup

  1. temperatureto reflux for one hour
  2. concentrationThe acetone was subsequently concentrated
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with petroleum ether
  6. customdried at 50° C

Sources & evidence

ORD record
ord-51e42b98d5594cadb8d84823a78e2621
Source dataset
uspto-grants-2001_04
Patent number
US06218406B1

Reaction notes

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