Sodium Hydroxide → HCID 18979176, compound

HRID 2393167Notes

Reaction equation

HRID 2393167 reaction equation
[C:1]([CH:3]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])#[N:2].[OH-].[Na+]>CO.O>[C:1]([CH:3]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18979205HCID 18979205, compound

Product 1

HCID 18979176HCID 18979176, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 50 ml of methanol was dissolved 7.38 g (25 mmol) of ethyl 6-cyano-6-(1-naphthyl)hexanoate followed by addition of 50 ml of iN aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was diluted with 150 ml of pure water and washed with 150 ml of ethyl acetate. The aqueous layer was acidified with 100 ml of 1 N HCl and extracted with 200 ml of ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and purified by silica gel column chromatography (hexane-ethyl acetate=1:4) to provide 6.66 g (yield 99.7%) of the title compound as colorless oil.

Workup

  1. washwashed with 150 ml of ethyl acetate
  2. extractionextracted with 200 ml of ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. custompurified by silica gel column chromatography (hexane-ethyl acetate=1:4)

Sources & evidence

ORD record
ord-3762c0a94e2f43198472373827d46c92
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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