Diethyl(methyl)silane → 1-(2-Hydroxy-2-methylpropoxy)-4-[3-(diethylmethylsilyl)propoxy]2,2,6,6-tetramethylpiperidine

HRID 843470Notes

Reaction equation

HRID 843470 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:13][CH2:14][C:15]([OH:18])([CH3:17])[CH3:16])[C:7]([CH3:20])([CH3:19])[CH2:6]1)[CH:2]=[CH2:3].[CH2:21]([SiH:23]([CH2:25][CH3:26])[CH3:24])[CH3:22]>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[OH:18][C:15]([CH3:17])([CH3:16])[CH2:14][O:13][N:8]1[C:7]([CH3:20])([CH3:19])[CH2:6][CH:5]([O:4][CH2:1][CH2:2][CH2:3][Si:23]([CH2:25][CH3:26])([CH2:21][CH3:22])[CH3:24])[CH2:10][C:9]1([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 69799Diethyl(methyl)silaneHCID 120843114-Allyloxy-1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidine

Product 1

HCID 697350151-(2-Hydroxy-2-methylpropoxy)-4-[3-(diethylmethylsilyl)propoxy]2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 28.5 g (0.10 mol) of the compound obtained in Example 17, 14.5 ml (0.10 mol) of diethylmethylsilane, and 1 ml of a solution of 2% hydrogen hexachloroplatinate(IV) in isopropyl alcohol is heated at reflux for 4 hours. The reaction mixture is distilled under vacuum to obtain a viscous, pale yellow oil. Mass spectroscopy reveals that the reaction product has a molecular ion of 387, which is consistent with formation of the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. distillationThe reaction mixture is distilled under vacuum
  4. customto obtain a viscous, pale yellow oil

Sources & evidence

ORD record
ord-e79a9cf5acbb44a3b06b19800fb8f810
Source dataset
uspto-grants-2002_04
Patent number
US06376584B1

Reaction notes

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