تفاعل #1340573

ord-2871bf8b840343a4aafa6e26c4a818be

معادلة التفاعل

CCOCCOCCOCCOc1cc(C#C[Si](C)(C)C)c(OCCOCCOCCOCC)cc1C#C[Si](C)(C)C
1,4-bis[(trimethylsilyl)ethynyl]-2,5-bis[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]benzene
[Na+].[OH-]
NaOH
O
Water
C#Cc1cc(OCCOCCOCCOC)c(C#C)cc1OCCOCCOCCOC
1,4-diethynyl-2,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzene

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةrefluxed for 2 hours
  2. 2
    استخلاصextracted with ether
  3. 3
    غسيلThe organic layer was washed with water several times
  4. 4
    تجفيفdried with Na2SO4
  5. 5
    أخرىSolvent was removed by rotary evaporation

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08455265B2uspto-grants-2013_06