Vinyltrimethoxysilane → HCID 59746997, compound

HRID 1955492Notes

Reaction equation

HRID 1955492 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:27][CH3:28])([O:25][CH3:26])[O:23][CH3:24])=[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:27][CH3:28])([O:25][CH3:26])[O:23][CH3:24])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 76004Vinyltrimethoxysilane2×HCID 110912Ethanone, 2-(1-methylethoxy)-1,2-diphenyl-

Product 1

HCID 59746997HCID 59746997, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.17 g (40 mmol) of benzoin isopropyl ether, 6.7 ml (44 mmol) of vinyltrimethoxysilane, 335 mg (0.4 mmol) of RuH2 (CO) (PPh3)3 and 75 ml of anhydrous toluene were mixed and stirred at reflux for 2 hours. At intervals of 2 hours, a further 3×200 mg (0.2 mmol) of RuH2 (CO) (PPh3)3 were added. The mixture was left to stand overnight, a further 200 mg (0.2 mmol) of RuH2 (CO) (PPh3)3 and 1 ml (6.6 mmol) of vinyltrimethoxysilane were added, the mixture was stirred at reflux for 8 hours, concentrated and worked up by chromatography (Florisil or silica gel, CH2Cl2 /ethyl acetate/heptane mixtures). 10.6 g of oil were obtained which after distillation in a bulb tube (220° C., 0.08 mbar) gave 9.0 g (56%) of a yellowish oil. 1H-NMR (DCDl3): 0.61-0.96 ppm (2H, mc, Et-H2); 1.21 ppm (6H, d, isopropyl-CH3, 3JH,H =6.2 Hz); 2.61 ppm (2H, mc, Et-H1); 3.53 ppm (9H, s, Si(OCH3)3); 3.71 ppm (1H, hept, sec. isopropyl-H); 5.55 ppm (1H, s, benzoin-H); 7.14-7.39 ppm (8H, m, Ph-H); 7.51 ppm (1H, dd, Ph-H6)

Workup

  1. temperatureat reflux for 2 hours
  2. waitThe mixture was left
  3. stirringthe mixture was stirred
  4. temperatureat reflux for 8 hours
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50c5d70bf3d4491290e830419166721a
Source dataset
uspto-grants-1998_07
Patent number
US05776658

Reaction notes

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