Potassium Carbonate → HCID 57150075, compound

HRID 466315Notes

Reaction equation

HRID 466315 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=[CH:17][C:16]=1[OH:28].[CH:29]1([CH2:35]Br)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C=O)C>[CH:29]1([CH2:35][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[C:15]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=[CH:17][C:16]=2[O:28][CH2:15][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:2]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 21734062HCID 21734062, compound

Product 1

HCID 57150075HCID 57150075, compoundYield 119.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5 ml of a DMF solution containing 250 mg (0.6477 mmol) of 2,2'-dihydroxy-5,5'-bis(3-methoxycarbonylpropyl) biphenyl and 0.920 ml (6.477 mmol) of cyclohexylmethyl bromide, there was added 360 ml (2.5907 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated overnight at 100° C. The reaction mixture was filtered by suction through Celite to remove the solid matter, which was washed with ethyl acetate. After the solvent in the filtrate had been evaporated off under reduced pressure, the evaporated residue was dissolved in chloroform. This solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, water and saline solution in this sequence and was dried over anhydrous sodium sulfate. The residue obtained after the solvent had been evaporated off was purified by silica gel column chromatography (with 12 g of WAKO-gel C-200, eluent: hexane and hexane/ethyl acetate of 25/1) to obtain 224 mg (0.3877 mmol, 60%) of 2,2'-dicyclohexylmethoxy-5,5'-bis(3-methoxycarbonylpropyl) biphenyl as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered by suction through Celite
  2. customto remove the solid matter, which
  3. washwas washed with ethyl acetate
  4. customAfter the solvent in the filtrate had been evaporated off under reduced pressure
  5. dissolutionthe evaporated residue was dissolved in chloroform
  6. washThis solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, water and saline solution in this sequence
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe residue obtained after the solvent
  9. customhad been evaporated off
  10. customwas purified by silica gel column chromatography (with 12 g of WAKO-gel C-200, eluent: hexane and hexane/ethyl acetate of 25/1)

Sources & evidence

ORD record
ord-22a3bb3ee6af453a8870516906ac6a4e
Source dataset
uspto-grants-1992_10
Patent number
US05155259

Reaction notes

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