Sodium Hydroxide → HCID 19348473, compound

HRID 1418200Notes

Reaction equation

HRID 1418200 reaction equation
[OH-].[Na+].[Si]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:19][C:20]([O:22]CC)=[O:21])=[C:14]([O:30][CH3:31])[CH:13]=1)(C(C)(C)C)(C)C>C(O)C>[OH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:19][C:20]([OH:22])=[O:21])=[C:14]([O:30][CH3:31])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19348492HCID 19348492, compound

Product 1

HCID 19348473HCID 19348473, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

80 ml of a 2N aqueous solution of sodium hydroxide were added to a solution of 32.64 g (77.2 mmol) of ethyl 3-(4-t-butyldimethylsilyloxymethyl-2-methoxyphenyl)octanoate [prepared as described in step (iv) above] in 80 ml of ethanol, and the resulting mixture was heated under reflux for 1 hour and 40 minutes. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the resulting residue was acidified with 2N aqueous hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, and then the solvent was removed by distillation under reduced pressure, to give 22.09 g (a quantitative yield) of the title compound as an oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour and 40 minutes
  3. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8da78e86c5074693ba4cf21c7420fd86
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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