Hydrochloric Acid → HCID 17816563, compound

HRID 2249659Notes

Reaction equation

HRID 2249659 reaction equation
IC.[CH2:3]([O:7][C:8]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:9]=1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:17]=1)=[O:11])[CH:4]([CH3:6])[CH3:5].[C:37](=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH2:3]([O:7][C:8]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]=[CH:28][C:9]=1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[C:16]([CH2:18][CH2:19][C:20]([O:22][CH3:37])=[O:21])[CH:17]=1)=[O:11])[CH:4]([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57684398HCID 57684398, compound

Product 1

HCID 17816563HCID 17816563, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At ambient temperature, 9.9 ml of iodomethane is dropwise added to a suspension of 50.0 g of 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoic acid and 22.0 g of potassium carbonate in 150 ml of N,N-dimethylformamide. The mixture thus obtained is stirred at the same temperature as above for 30 minutes. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 51.0 g of methyl 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate as a light brown-colored solid product.

Workup

  1. customThe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0b9a291c862b4bd1aa3fb53ff2dda02d
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…