4-Iodophenol → HCID 55253204, compound

HRID 384094Notes

Reaction equation

HRID 384094 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[C:10]#[CH:11]>CN(C)C=O.[Cu-]=O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 108944-IodophenolHCID 12182Ethyl propiolate

Product 1

HCID 55253204HCID 55253204, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-iodophenol (22.3 g) in dimethylformamide (200 ml) were added 19.5 ml of ethyl propiolate and 14.8 g of copper (I) oxide, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then filtered through Celite, and the filtrate was vacuum-concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)), followed by recrystallization of the purified residue with hexane/ethyl acetate to afford the title compound as a white solid.

Workup

  1. temperatureThe reaction solution was cooled
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was vacuum-concentrated
  4. customThe residue obtained
  5. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1))
  6. customfollowed by recrystallization of the purified residue with hexane/ethyl acetate

Sources & evidence

ORD record
ord-485ae005c57144b5835bfeb50a0d2a22
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…