Isopropylamine → (E)(E) 2,7-bis-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-fluoren-9-one

HRID 1353193Notes

Reaction equation

HRID 1353193 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[CH3:17]/[C:18](/[C:22]#[CH:23])=[CH:19]\[CH2:20][OH:21].[CH:24](N)(C)[CH3:25].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>[Cu]I.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>[OH:21][CH2:20]/[CH:19]=[C:18](\[CH3:17])/[C:22]#[C:23][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([C:24]#[C:25]/[C:29](/[CH3:30])=[CH:28]/[CH2:32][OH:31])=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 8028TetrahydrofuranHCID 2599222,7-Dibromo-9-fluorenoneHCID 53676041-Pentol, (E)-

Product 1

HCID 86588418(E)(E) 2,7-bis-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-fluoren-9-oneYield 71%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 2,7-dibromo-9-fluorenone (338 mg, 1.0 mmol) in dry THF (17 mL) under a nitrogen atmosphere were added copper(I) iodide (30 mg, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium (II) (70 mg, 0.10 mmol), trans-3-methyl-2-penten-4-yn-1-ol (481 mg, 5.0 mmol) and dry isopropylamine (17 mL). After stirring at room temperature for 6 h, the reaction mixture was filtered and the filtrate evaporated to dryness. The product was purified by column chromatography on silica using dichloromethane/THF (10:1) as eluent to give 200 mg (71%) of (E)(E) 2,7-bis-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-fluoren-9-one.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. customThe product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-385aa9adc1114d78bb39921a6a4f89bb
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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