Hydrochloric Acid → HCID 22420868, compound

HRID 1440994Notes

Reaction equation

HRID 1440994 reaction equation
[O:1]=[C:2]([CH:8]([CH2:14][CH2:15][Si:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O>[CH3:24][Si:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:17])[CH2:15][CH2:14][CH2:8][C:2](=[O:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723671Tetrabutylammonium HydroxideHCID 15332544HCID 15332544, compound

Product 1

HCID 22420868HCID 22420868, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask were placed 27.1 g (0.0773 mole) of diethyl 2-oxo-3-(3-methyl-3-phenyl-3-silabutyl)succinate, 301 g (0.464 mole) of 40 wt % tetrabutyl ammonium hydroxide, and 500 mL of water. This mixture was heated at reflux under a nitrogen atmosphere for 25 minutes after which it was cooled to ambient temperature. The reaction mixture was acidified with 50 mL of 12N hydrochloric acid and then extracted twice with 400 mL of diethyl ether. The extracts were combined and washed with 100 mL of 3N hydrochloric acid after which the solvent was evaporated under reduced pressure, yielding 17.45 g of 6-methyl-6-phenyl-2-oxo-6-silaheptanoic acid as an oil.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated
  3. temperatureat reflux under a nitrogen atmosphere for 25 minutes after which it
  4. extractionextracted twice with 400 mL of diethyl ether
  5. washwashed with 100 mL of 3N hydrochloric acid after which the solvent
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c90f87692714df48bcc4ba65cfc7085
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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