Water → 6-Ethoxy-2-nitro-3-phenyl-1-benzofuran

HRID 2397878Notes

Reaction equation

HRID 2397878 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:21]=[CH:20][C:7]2[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:9]([N+:11]([O-:13])=[O:12])[O:10][C:6]=2[CH:5]=1.[CH2:22](I)[CH3:23].O>C(COC)OC>[CH2:22]([O:3][C:4]1[CH:21]=[CH:20][C:7]2[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:9]([N+:11]([O-:13])=[O:12])[O:10][C:6]=2[CH:5]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 20195525HCID 20195525, compound

Product 1

HCID 214367776-Ethoxy-2-nitro-3-phenyl-1-benzofuran

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of 0.34 g (0.008 mole) of sodium hydride in 45 ml of glyme is added dropwise a solution of 2.0 g (0.008 mole) of 6-hydroxy-2-nitro-3-phenylbenzofuran in 20 ml of glyme. To this suspension is added 16 g (0.010 mole) of ethyl iodide and the mixture is heated to its reflux temperature and maintained at reflux for 5 hours. After cooling to 25° C. an additional 0.1 g of sodium hydride and 5 ml of ethyl iodide are added and the mixture is refluxed for about three hours. The mixture is poured into water and extracted with diethyl ether. The extracts are washed with water and saturated sodium chloride solution and dried. Concentration of the extracts provides a residue which is recrystallized from aqueous ethanol to provide yellow needles of 6-ethoxy-2-nitro-3-phenylbenzofuran, m.p. 109°-111° C.

Workup

  1. temperaturethe mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for 5 hours
  5. additionare added
  6. temperaturethe mixture is refluxed for about three hours
  7. extractionextracted with diethyl ether
  8. washThe extracts are washed with water and saturated sodium chloride solution
  9. customdried
  10. customConcentration of the extracts provides a residue which
  11. customis recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-825101c527774138b83f688251c6837a
Source dataset
uspto-grants-1977_05
Patent number
US04022908

Reaction notes

Loading…