Vinyltriethoxysilane → HCID 59747005, compound

HRID 1955493Notes

Reaction equation

HRID 1955493 reaction equation
[CH:1]([O:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[CH:20]([Si:22]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH2:21]>C1(C)C=CC=CC=1>[CH:1]([O:4][CH:5]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:21][CH2:20][Si:22]([O:23][CH2:24][CH3:25])([O:26][CH2:27][CH3:28])[O:29][CH2:30][CH3:31])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6516Vinyltriethoxysilane2×HCID 110912Ethanone, 2-(1-methylethoxy)-1,2-diphenyl-

Product 1

HCID 59747005HCID 59747005, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.2 g (40 mmol) of benzoin isopropyl ether, 9.2 ml (44 mmol) of vinyltriethoxysilane and 735 mg (0.8 mmol) of RuH2 (CO) (PPh3)3 were dissolved in 60 ml of anhydrous toluene and degassed by passing in argon for 1/2 hour. The mixture was then stirred with exclusion of light and under argon, at reflux, for 7 hours and left to stand overnight at room temperature, a further 370 mg (0.4 mmol) of RuH2 (CO) (PPh3)3 and 1 ml (5 mmol) of vinyltriethoxysilane were added, and heating at reflux was carried out for a further 6.5 hours. After the toluene had been distilled off, the mixture was chromatographed on silica gel (initially heptane/CH2Cl2 9:1, then CH2 Cl2, then CH2Cl2 /ethyl acetate, finally ethyl acetate) and purified by bulb-tube distillation. 9.8 g (55%) of a pale yellowish oil were obtained. 1H-NMR (CDCl3): 0.61-0.95 ppm (2H, mc, Et-H2); 1.21 ppm (6H, d, isopropyl-CH3, 3JH,H =6.0 Hz); 1.22 ppm (9H, t, ethoxy-CH3, 3JH,H =7.0 Hz); 2.61 ppm (2H, mc, Et-H1); 3.71 ppm (1H, hept, isopropyl-H); 3.79 ppm (6H, q, ethoxy-CH2); 5.55 ppm (1H, s, benzoin-H); 7.13-7.38 ppm (8H, m, Ph-H); 7.48 ppm (1H, dd, Ph-H6, 3JH5,H6 =7.6 Hz).

Workup

  1. customdegassed
  2. temperatureat reflux, for 7 hours
  3. waitleft
  4. waitto stand overnight at room temperature
  5. temperatureheating
  6. temperatureat reflux
  7. waitwas carried out for a further 6.5 hours
  8. distillationAfter the toluene had been distilled off
  9. customthe mixture was chromatographed on silica gel (initially heptane/CH2Cl2 9:1
  10. customCH2 Cl2, then CH2Cl2 /ethyl acetate, finally ethyl acetate) and purified by bulb-tube
  11. distillationdistillation

Sources & evidence

ORD record
ord-280ffa6215d84ddd98cdb40ad1772f4a
Source dataset
uspto-grants-1998_07
Patent number
US05776658

Reaction notes

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