Tetrahydrofuran → HCID 18987477, compound

HRID 2396560Notes

Reaction equation

HRID 2396560 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](O)=O)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[C:20](Cl)(=[O:24])C(Cl)=O.C1C[O:29]CC1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][C:20]([OH:24])=[O:29])=[C:7]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 189874615-Chloro-3-phenyl-1-benzofuran-2-carboxylic acid

Product 1

HCID 18987477HCID 18987477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a solution of 5-chloro-3-phenylbenzofuran-2-carboxylic acid (0.66 g) in anhydrous THF (15 ml) were added oxalyl chloride (0.30 ml) and DMF (one drop) at room temperature. The mixture was stirred for 0.5 hour. The solvent was distilled off, and the residue (containing the acid chloride) was dissolved in anhydrous THF (10 ml). To this solution was added an ethyl ether solution of diazomethane (prepared from 1.5 g of N-nitrosomethyl urea). The mixture was stirred for 0.5 hour at room temperature. The solvent was distilled off, and the residue (containing the diazoketone compound) was dissolved in methanol (20 ml). To the solution was added portionwise silver oxide (Ag2O) (0.20 g), while stirring at 50° C. This mixture was stirred with heating under reflux for 3 hours, which was then subjected to filtration with celite. From the filtrate was distilled off the solvent. The residue was purified by means of a silica gel (30 g) column chromatography (hexane - ethyl acetate=5:1) to afford methyl ester of 5-chloro-3-phenylbenzofuran-2-acetic acid as a pale yellow oily product (0.44 g)

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue (containing the acid chloride)
  3. dissolutionwas dissolved in anhydrous THF (10 ml)
  4. additionTo this solution was added an ethyl ether solution of diazomethane (prepared from 1.5 g of N-nitrosomethyl urea)
  5. stirringThe mixture was stirred for 0.5 hour at room temperature
  6. distillationThe solvent was distilled off
  7. additionthe residue (containing the diazoketone compound)
  8. dissolutionwas dissolved in methanol (20 ml)
  9. additionTo the solution was added portionwise silver oxide (Ag2O) (0.20 g)
  10. stirringwhile stirring at 50° C
  11. stirringThis mixture was stirred
  12. temperaturewith heating
  13. temperatureunder reflux for 3 hours
  14. filtrationwhich was then subjected to filtration with celite
  15. distillationFrom the filtrate was distilled off the solvent
  16. customThe residue was purified by means of a silica gel (30 g) column chromatography (hexane - ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0fb7f0198b654f6bb030c2c1ccd4860d
Source dataset
uspto-grants-1996_02
Patent number
US05492929

Reaction notes

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