Ethyl propiolate → Ethyl 3-(4-((6-phenoxypyridin-2-yl)methoxy)phenyl)prop-2-enoate

HRID 384103Notes

Reaction equation

HRID 384103 reaction equation
I[C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[C:24]#[CH:25]>CN(C)C=O.[Cu]=O>[O:14]([C:10]1[N:9]=[C:8]([CH2:7][O:6][C:5]2[CH:21]=[CH:22][C:2]([CH:25]=[CH:24][C:23]([O:27][CH2:28][CH3:29])=[O:26])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 12182Ethyl propiolateHCID 684313182-((4-Iodophenoxy)methyl)-6-phenoxypyridine

Product 1

HCID 68431100Ethyl 3-(4-((6-phenoxypyridin-2-yl)methoxy)phenyl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-((4-iodophenoxy)methyl)-6-phenoxypyridine (160 mg) in dimethylformamide (2 ml), 0.116 ml of ethyl propiolate and 69 mg of copper (II) oxide were added, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then Celite-filtered, and the filtrate was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (0:100-20:80-33/67)) to afford the title compound as a colorless oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. filtrationCelite-filtered
  3. distillationthe filtrate was distilled off under reduced pressure
  4. customThe residue obtained
  5. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (0:100-20:80-33/67))

Sources & evidence

ORD record
ord-f89665843c004c2aa9b4650adccf7157
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…