Hydrochloric Acid → 4,5-difluoro-7-pentyl-2-(4-propylphenyl)-8,9-dihydro-7H-furo[3,2-f]chromene

HRID 2244855Notes

Reaction equation

HRID 2244855 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4](I)[C:3]=1[OH:19].C([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][CH3:30])#C.Cl.[CH2:32](N(CC)CC)[CH3:33]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]2[CH:32]=[C:33]([C:26]3[CH:27]=[CH:22][C:23]([CH2:28][CH2:29][CH3:30])=[CH:24][CH:25]=3)[O:19][C:3]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 22052971Ethynyl-n-propylbenzeneHCID 592152577,8-Difluoro-5-iodo-2-pentylchroman-6-ol

Product 1

HCID 592152944,5-difluoro-7-pentyl-2-(4-propylphenyl)-8,9-dihydro-7H-furo[3,2-f]chromene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

2.0 g (5.23 mmol) of 7,8-difluoro-5-iodo-2-pentylchroman-6-ol are firstly stirred for 6 h at 60° C. together with 1.13 g (7.85 mmol) of ethynyl-n-propylbenzene in the presence of 110 mg (0.16 mmol) of bis(triphenylphosphine)palladium(II) chloride and 30 mg (0.16 mmol) of copper(I) iodide in 22 ml of triethylamine. The mixture is subsequently refluxed for 18 h. After cooling, the batch is added to ice/water and acidified using hydrochloric acid. The mixture is extracted a number of times with MTBE, and the combined extracts are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2,

Workup

  1. temperatureThe mixture is subsequently refluxed for 18 h
  2. temperatureAfter cooling
  3. extractionThe mixture is extracted a number of times with MTBE
  4. washthe combined extracts are washed with water and sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2

Sources & evidence

ORD record
ord-11954e2aaa5f443e9b83eafb4703cb91
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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