Trimethylsilane → 4-(1-Trimethylsilylhexyloxy)phenyl 4-(1-trimethylsilylbutyloxy)benzoate

HRID 1197725Notes

Reaction equation

HRID 1197725 reaction equation
[CH2:1]([O:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[CH3:28][SiH:29]([CH3:31])[CH3:30]>ClCCl.C1([Pt](Cl)(Cl)C2C=CC=C2)C=CC=C1>[CH3:28][Si:29]([CH3:31])([CH3:30])[CH:1]([O:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH:20]([Si:29]([CH3:31])([CH3:30])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:18]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 70435TrimethylsilaneHCID 199721374-(5-Hexenyloxy)phenyl 4-(3-butenyloxy)benzoate

Product 1

HCID 191044944-(1-Trimethylsilylhexyloxy)phenyl 4-(1-trimethylsilylbutyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 178479810HCID 178479810, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.35 g (0.01 mmol of Pt) of L.5% strength dicyclopentadienylplatinum dichloride solution in dichloromethane was added as catalyst to a solution of 5.00 g (9.71 mmol) of 4-(5-hexenyloxy)phenyl 4-(3-butenyloxy)benzoate in 10 ml of dichloromethane, and 2.02 g (27.2 mmol) of trimethylsilane were passed into the refluxing mixture over the course of 8 hours. After complete hydrosilylation of the olefin, the reaction mixture was flushed with nitrogen, and the dichloromethane was removed by vacuum distillation on a rotary evaporator. The crude product was purified by chromatography on silica gel, to give 4-(1-trimethylsilylhexyloxy)phenyl 4-(1-trimethylsilylbutyloxy)benzoate, phases: c 72 i.

Workup

  1. customwere passed into the refluxing mixture over the course of 8 hours
  2. customAfter complete hydrosilylation of the olefin, the reaction mixture was flushed with nitrogen
  3. customthe dichloromethane was removed by vacuum distillation on a rotary evaporator
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e2f6d6b83bba4bdf8f1698a3c647b36a
Source dataset
uspto-grants-1994_01
Patent number
US05277838

Reaction notes

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