Dimethylformamide → HCID 23242191, compound

HRID 466313Notes

Reaction equation

HRID 466313 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=[CH:17][C:16]=1[OH:28].CI.[C:31](=O)([O-])[O-].[K+].[K+].CN([CH:40]=[O:41])C>[Cu]>[CH3:31][O:28][C:16]1[CH:17]=[CH:18][C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][C:15]=1[C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[O:41][CH3:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21734064HCID 21734064, compound

Product 1

HCID 23242191HCID 23242191, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

To 5 ml of a DMF solution containing 200 mg (0.05181 mmol) of 2,2'-dihydroxy-5,5'-bis(2-ethoxycarbonylethyl) biphenyl and 2.316 ml (20.72 mmol) of methyl iodide, there was added 572 mg (2.072 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated for 4 days at room temperature and for a further 2 days at 60° 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 was 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 20 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 50/1) to obtain 182 mg (0.4936 mmol, 85%) of 2,2'-dimethoxy-5,5'-bis(2-ethoxycarbonylethyl) biphenyl as an oily product.

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 was 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 20 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 50/1)

Sources & evidence

ORD record
ord-3c2540708e9b4297af23321148472ca6
Source dataset
uspto-grants-1992_10
Patent number
US05155259

Reaction notes

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