Ethanol → HCID 86639775, compound

HRID 555217Notes

Reaction equation

HRID 555217 reaction equation
[CH3:1][O:2][Si:3]([C:8]12[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH:10]=[CH:9]2)([O:6][CH3:7])[O:4][CH3:5].C([SiH]([CH2:20][CH3:21])CC)C.[CH2:22](O)[CH3:23]>ClCCl.C1COCC1.C1(C)C=CC=CC=1>[CH2:22]([C:8]12[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH:10]=[CH:9]2)[CH2:23][CH2:20][CH3:21].[CH3:1][O:2][Si:3]([C:8]12[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH:10]=[CH:9]2)([O:4][CH3:5])[O:6][CH3:7]

Participants

7

Reactant 3

HCID 702EthanolHCID 12052TriethylsilaneHCID 21946567HCID 21946567, compound2×

Product 1

HCID 86639775HCID 86639775, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

BuNB (10.97 g, 0.073 mol), TrimethoxysilylNorbornene (TMSNB, CAS 7538-46-7) (12.95 g, 0.073 mol), triethyl silane (0.34 g, 2.91E-04 mol), ethanol (0.80 g, 1.75E-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 Pd1446 (0.017 g, 1.16E-05 mol) and DANFABA (0.028 g, 3.49E-5 mol), each in the form of a concentrated solution in dichloromethane. After addition, the resulting mixture was maintained at 80° C. for 4 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, 15.5 g was obtained (65%). The molecular weight of the copolymer was determined by GPC in THF solvent (polystyrene standard) to be Mw=48,000 and Mn=27,000. The composition of the copolymer was determined by 1H-NMR to be (47/53) BuNB/TMSNB copolymer. The refractive indices of this polymer were measured by prism coupling method and determined to be 1.5093 in TE mode and 1.5089 in TM mode at a wavelength of 633 nm. 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 4 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. custom15.5 g was obtained (65%)
  11. customto result in a 30 wt % copolymer solution

Sources & evidence

ORD record
ord-0ca213d8a64741d48b02abfadffbe330
Source dataset
uspto-grants-2011_11
Patent number
US08053166B2

Reaction notes

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