Ethanol → HCID 86639774, compound

HRID 1965907Notes

Reaction equation

HRID 1965907 reaction equation
[CH2:1]([O:3][Si:4]([C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].C([SiH]([CH2:23][CH3:24])CC)C.[CH2:25](O)[CH3:26]>ClCCl.C1COCC1.C1(C)C=CC=CC=1>[CH2:25]([C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)[CH2:26][CH2:23][CH3:24].[CH2:6]([O:5][Si:4]([C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

7

Reactant 3

HCID 702EthanolHCID 12052TriethylsilaneHCID 21584945HCID 21584945, compound2×

Product 1

HCID 86639774HCID 86639774, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

BuNB (25.22 g, 0.168 mol), Triethoxysilyl Norbornene (TESNB, CAS 18401-43-9) (4.78 g, 0.019 mol), triethyl silane (0.011 g, 9.32E-05 mol), ethanol (0.10 g, 2.24E-03 mol) and toluene (170.0 g) were combined in a 500 mL serum bottle and heated to 80° C. in an oil bath to form a solution. To this solution were injected Pd1206 (0.018 g, 1.49E-05 mol) in the form of a concentrated solution in dichloromethane. After addition, the resulting mixture was maintained at 80° C. for 9 hours. The copolymer was precipitated by adding methanol drop wise into the vigorously stirred reaction mixture. The precipitated copolymer was collected by filtration and dried in an oven at 60° C. under vacuum. After drying, 20.58 g was obtained (69%). The molecular weight of the copolymer was determined by GPC in THF solvent (polystyrene standard) to be Mw=238,000 and Mn=96,000. The composition of the copolymer was determined by 1H-NMR to be (85/15) BuNB/TESNB copolymer. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5061 in TE mode and 1.5041 in TM mode at a wavelength of 633 nm. The Tg (based on thermomechanical analysis (TMA) measurement) of this polymer was 276° C. The dried copolymer was dissolved in sufficient toluene to result in a 30 wt % copolymer solution.

Workup

  1. customto form a solution
  2. additionAfter addition
  3. temperaturethe resulting mixture was maintained at 80° C. for 9 hours
  4. customThe copolymer was precipitated
  5. additionby adding methanol
  6. customdrop wise into the vigorously stirred reaction mixture
  7. filtrationThe precipitated copolymer was collected by filtration
  8. customdried in an oven at 60° C. under vacuum
  9. customAfter drying
  10. custom20.58 g was obtained (69%)
  11. customwas 276° C
  12. customto result in a 30 wt % copolymer solution

Sources & evidence

ORD record
ord-91a2d0276a7849b282e30ae80481482d
Source dataset
uspto-grants-2013_04
Patent number
US08420293B2

Reaction notes

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