HCID 14579738, compound → HCID 14579736, compound

HRID 1534233Notes

Reaction equation

HRID 1534233 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([F:11])[C:5]=2[O:4][C:3]=1C(O)=O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([CH2:12][CH2:13][CH3:14])[CH:9]=[C:10]([F:11])[C:5]=2[O:4][CH:3]=1

Participants

4

Reactant 1

HCID 14579738HCID 14579738, compound

Product 1

HCID 14579736HCID 14579736, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A mixture of 3-methyl-4-hydroxy-5-propyl-7-fluorobenzofurancarboxylic acid (0.10 gm; 0.4 mmoles) and copper(20 mg) in quinoline (50 mL) was refluxed for a period of 2.5 hours. The two phases were separated and the organic phase was dried (Na2SO4), and concentrated in vacuo. The residue was purified by preparative TLC and eluted with 5% ethylacetate in hexane to yield 3-methyl-4-hydroxy-5-propyl-7-fluorobenzofuran (62 mg; 75%), identical to the product obtained from the cyclisation reaction described above in step f.

Workup

  1. temperaturewas refluxed for a period of 2.5 hours
  2. customThe two phases were separated
  3. dry with materialthe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC
  6. washeluted with 5% ethylacetate in hexane

Sources & evidence

ORD record
ord-e59f5ea6d62946e4acbb858c8a9c4c7f
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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