Iodoethane → HCID 54370545, compound

HRID 846485Notes

Reaction equation

HRID 846485 reaction equation
[OH:1][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].[CH2:29](I)[CH3:30].C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C=O)C>[CH2:29]([O:1][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])[CH3:30]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21734064HCID 21734064, compound

Product 1

HCID 54370545HCID 54370545, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5 ml of a DMF solution containing 200 mg (0.5181 mmol) of 2,2'-dihydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl and 0.423 ml (5.181 mmol) of ethyl iodide, there were added 85.8 mg (0.6217 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated overnight at room temperature. The reaction mixture was filtered by suction through Celite to remove the solid matte rand the filtrate 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 aqueous sodium chloride solution in this sequence and was dried by adding 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 100/1 and 75/1) to obtain 141.6 mg (0.3420 mmol, 66%) of 2-ethoxy-2'-hydroxy-5,5'-bis (2-ethoxycarbonylethyl) biphenyl as an oily product. 1H-NMR (CDCl3) δ (ppm): 1.24 (6H, t, 2CH3), 1.36 (3H, t, CH3), 2.62 (2H, t, CH2), 2.63 (2H, t, CH2), 2.94 (2H, t, CH2), 2.95 (2H, t, CH2), 4.11 (`6H, q, CH2), 4.13 (4H, q, 2CH2), 6.66 (1H, s, OH), 6.9-7.3 (6H, m, arom-H) MS (FAB): 414 (M+)

Workup

  1. filtrationThe reaction mixture was filtered by suction through Celite
  2. customto remove the solid matte rand the filtrate
  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 aqueous sodium chloride solution in this sequence
  7. customwas dried
  8. additionby adding anhydrous sodium sulfate
  9. customThe residue obtained after the solvent
  10. customhad been evaporated off
  11. customwas purified by silica gel column chromatography (with 20 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1 and 75/1)

Sources & evidence

ORD record
ord-8b2f6b668885428c988ea4c4514fcd5d
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

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