Potassium Carbonate → HCID 53712141, compound

HRID 846495Notes

Reaction equation

HRID 846495 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].Br[CH:30]([Cl:33])[CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C=O)C>[Cl:33][CH2:30][CH2:31][CH2:32][O: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]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 21734062HCID 21734062, compound

Product 1

HCID 53712141HCID 53712141, compound

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 (3-methoxycarbonylpropyl) biphenyl and 0.646 ml (5.181 mmol) of 1-bromo-chloropropane, 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 for 5 hours at room temperature. The reaction mixture was filtered by suction through Celite to remove the solid matter and 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 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 15 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1) to obtain 206 mg (0.4454 mmol, 86%) of 2-(3-chloropropoxy-2' -hydroxy-5,5'-bis (3-methoxycarbonylpropyl) biphenyl as an oily product. 1H-NMR (CDCl3) δ (ppm): 1.8-2.2 (6H, m, 3CH2), 2.36 (4H, t, 2CH2), 2.5-2.8 (4H, m, 2CH2), 3.51 (2H, t, CH2), 3.66 (6H, s, 2CH3), 4.16 (2H, t, CH2), 6.05 (1H, s, OH), 6.8-7.3 (6H, m, arom-H) MS (FAB): 461 (M-H)-

Workup

  1. filtrationThe reaction mixture was filtered by suction through Celite
  2. customto remove the solid matter
  3. washthe filtrate was 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
  7. additionwith dilute hydrochloric sodium chloride solution in this sequence
  8. customwas dried
  9. additionby adding anhydrous sodium sulfate
  10. customThe residue obtained after the solvent
  11. customhad been evaporated off
  12. customwas purified by silica gel column chromatography (with 15 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1)

Sources & evidence

ORD record
ord-09e8bd2c877a4d2dae3df34b9a8995ba
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

Loading…