Potassium Hydroxide → HCID 86678075, compound

HRID 2369759Notes

Reaction equation

HRID 2369759 reaction equation
[CH2:1]([C:5]1([CH2:30][CH2:31][CH2:32][CH3:33])[C:17]2[CH:16]=[C:15]([C:18]#[C:19]C(C)(O)C)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([C:24]#[C:25]C(C)(O)C)=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>C1(C)C=CC=CC=1.CC(O)C>[C:24]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:17](=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=3)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:30][CH2:31][CH2:32][CH3:33])[C:6]=2[CH:7]=1)#[CH:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67260290HCID 67260290, compound

Product 1

HCID 86678075HCID 86678075, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21881414Toluene isopropyl alcoholSolvent

Procedure

To a solution of 4,4′-(9,9-dibutyl-9H-fluorene-2,7-diyl)bis(2-methyl-3-butyn-2-ol) (1.04 g, 2.35 mmol) in 20 mL of toluene/i-PrOH (3/1), was added solid KOH (0.39 g). The mixture was heated under reflux for 0.5 h. After cooling, KOH was filtered off and the solvents were evaporated and the residue was purified by column chromatography (heptane/CH2Cl2 70:30 then 20:80) to yield 0.54 g (71%) of 2,7-diethynyl-9,9-dibutyl-9H-fluorene: 1H NMR (200.13 MHz, CDCl3) δ 7.63 (d, J=8.6 Hz, 2H), 7.48 (d, J=8.6 Hz, 2H), 7.46 (s, 2H), 3.15 (s, 2H), 1.94 (m, 4H), 1.07 (m, 4H), 0.67 (t, J=7.2 Hz, 6H), 0.54 (m, 4H); 13C NMR (50.32 MHz, CDCl3) δ 151.0, 140.9, 131.2, 126.5, 120.8, 119.9, 84.5, 77.4, 55.1, 40.0, 25.8, 22.9, 13.7; HRMS (EI) calcd for C25H26 (M+·) m/z 326.2035. found 326.2036. Anal. Calcd for C25H26 (326.48): C, 91.97; H, 8.03. Found: C, 92.17; H, 8.07.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 0.5 h
  3. temperatureAfter cooling
  4. filtrationKOH was filtered off
  5. customthe solvents were evaporated
  6. customthe residue was purified by column chromatography (heptane/CH2Cl2 70:30

Sources & evidence

ORD record
ord-39743ddb72004b689bfec63db18ed96c
Source dataset
uspto-grants-2014_04
Patent number
US08709747B2

Reaction notes

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