Sodium Hydroxide → HCID 86692523, compound

HRID 1748576Notes

Reaction equation

HRID 1748576 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([Br:19])=[CH:14][N:13]=2)=[CH:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C.O1CCCC1>[Br:19][C:15]1[CH:16]=[C:17]([CH3:18])[C:12]([C:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH:8]=2)=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86692524HCID 86692524, compound

Product 1

HCID 86692523HCID 86692523, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of [4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]carboxylic acid ethyl ester (8.57 g) in ethanol (26 ml) and tetrahydrofuran (26 ml) was added 2N aqueous solution of sodium hydroxide (52 ml) at room temperature, and stirred at 70° C. for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, and extracted with diethyl ether. To the obtained aqueous layer was added 1 N hydrochloric acid aqueous solution under ice-cooling, and the precipitated solid was collected by filtration to give [4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]carboxylic acid (5.37 g) as a pale yellow solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with diethyl ether
  4. additionTo the obtained aqueous layer was added 1 N hydrochloric acid aqueous solution under ice-
  5. temperaturecooling
  6. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-6f93ccfe84c542cc8bc04d8cfea1971b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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