Potassium Carbonate → HCID 19744863, compound

HRID 2254221Notes

Reaction equation

HRID 2254221 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:15](=[O:26])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>CC(C)=O>[CH3:14][O:13][C:6]1[CH:5]=[CH:4][C:3]([C:15](=[O:26])[CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[C:2]([O:1][CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:7]=1[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 14368066HCID 14368066, compound

Product 1

HCID 19744863HCID 19744863, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Then, 21.5 g of 1-(2-hydroxy-4-methoxy-3-isopentylphenyl)-3-(4-methoxyphenyl)-1-propanone was dissolved in 150 ml of anhydrous acetone, and 41.6 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred for 30 minutes. Then, 18.4 g of methyl α-bromoacetate was added to the reaction mixture, and the mixture was stirred at room temperature for 5 days to effect reaction. After the reaction, the reaction mixture was extracted with diethyl ether and the solvent was removed from the extract, and the obtained residue was subjected to the silica gel chromatography (eluting solvent: n-hexane/ethyl acetate=8/1) to obtain 20.9 g (yield=80.9%) of 1-(4-methoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(4-methoxyphenyl)-1-propanone in the form of a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 days
  2. customreaction
  3. customAfter the reaction
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. customthe solvent was removed from the extract
  6. washthe obtained residue was subjected to the silica gel chromatography (eluting solvent: n-hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-2534d96447ae4fd0ae57988b72f42b0f
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

Loading…