Water → 1,4-Diethynyl-2,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzene

HRID 1253391Notes

Reaction equation

HRID 1253391 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23]C)[C:10]([C:25]#[C:26][Si](C)(C)C)=[CH:9][C:8]=1[O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41]C)(C)C.[OH-].[Na+].O>C1COCC1.CO>[C:25]([C:10]1[CH:9]=[C:8]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH3:41])[C:7]([C:6]#[CH:5])=[CH:12][C:11]=1[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])#[CH:26]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67251592HCID 67251592, compound

Product 1

HCID 251276271,4-Diethynyl-2,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,4-bis[(trimethylsilyl)ethynyl]-2,5-bis[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]benzene (0.595 g, 1 mmol) was dissolved in 20 mL of THF and 10 mL of methanol. To the solution, 8 mL of 1M NaOH(aq) was added and refluxed for 2 hours. Water was added to the mixture and extracted with ether. The organic layer was washed with water several times, and then dried with Na2SO4. Solvent was removed by rotary evaporation to give 1,4-diethynyl-2,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene (3), shown in FIG. 2, as a reddish solid. 1H NMR (300 MHz, CDCl3): d 3.32 (s, 2H), 3.36 (s, 6H), 3.53 (m, 4H), 3.65 (m, 8H), 3.75 (m, 4H), 3.85 (m, 4H), 4.13 (m, 4H), 6.98 (s, 2H). 13C NMR (75 MHz, CDCl3): d 59.46, 69.96, 70.03, 71.00, 71.15, 71.50, 72.39, 80.00, 83.22, 114.02, 118.75, 154.49.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed with water several times
  4. dry with materialdried with Na2SO4
  5. customSolvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-2871bf8b840343a4aafa6e26c4a818be
Source dataset
uspto-grants-2013_06
Patent number
US08455265B2

Reaction notes

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