Water → Hexamethyldisiloxane

HRID 2253560Notes

Reaction equation

HRID 2253560 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[OH2:10]>ClCCl>[CH3:1][Si:2]([O:10][Si:2]([CH3:9])([CH3:8])[CH3:1])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 962WaterHCID 28925(Trimethylsilyl)imidazole

Product 1

HCID 24764HexamethyldisiloxaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the alcohol 18 (200 mg) and N-(trimethylsilyl)imidazole (0.714 ml) in dichloromethane (13 ml) is stirred at room temperature for 16 hours. After water (4.9 ml) has been added, the mixture is left stirring for 20 minutes. The mixture is then extracted with ethyl acetate. The organic phases are washed with brine and dried. After concentration under vacuum, the residue is purified by chromatography on silica gel (230-400 mesh) (12% diethyl ether in hexane), to give 200 mg of derivative 15b (80% yield).

Workup

  1. waitthe mixture is left
  2. extractionThe mixture is then extracted with ethyl acetate
  3. washThe organic phases are washed with brine
  4. customdried
  5. concentrationAfter concentration under vacuum
  6. customthe residue is purified by chromatography on silica gel (230-400 mesh) (12% diethyl ether in hexane)

Sources & evidence

ORD record
ord-38714b17a18544ee8d2feaf74fd01636
Source dataset
uspto-grants-1993_08
Patent number
US05232836

Reaction notes

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