Potassium Hydroxide → 5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoic acid

HRID 1052894Notes

Reaction equation

HRID 1052894 reaction equation
[CH2:1]([O:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:10][CH2:11][CH2:12][C:13](N1CCOCC1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:28].[K+]>C(O)(C)C>[CH2:1]([O:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:10][CH2:11][CH2:12][C:13]([OH:14])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 667126875-Benzyloxy-5-(4-fluoro-phenyl)-1-morpholin-4-yl-pentan-1-one

Product 1

HCID 667130465-Benzyloxy-5-(4-fluoro-phenyl)-pentanoic acidYield 79.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10 gms of 5-Benzyloxy-5-(4-fluoro-phenyl)-1-morpholin-4-yl-pentan-1-one was added to 100 ml of isopropyl alcohol and 7.5 gms of potassium hydroxide. Heated the reaction mass at reflux temperature and maintain for about 36 hours and distilled off solvent completely. To the obtained oily mass 60 ml of water was added and washed with dichloromethane. Layers were separated and acidify the aqueous layer with hydrochloric acid and adjusted the pH to 2.0. The obtained aqueous layer was extracted with dichloromethane and dried the organic layer over sodium sulphate followed by concentration. 6.5 gms of 5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoic acid was isolated in heptane.

Workup

  1. temperatureHeated the reaction mass
  2. temperatureat reflux temperature
  3. temperaturemaintain for about 36 hours
  4. distillationdistilled off solvent completely
  5. additionTo the obtained oily mass 60 ml of water was added
  6. washwashed with dichloromethane
  7. customLayers were separated
  8. extractionThe obtained aqueous layer was extracted with dichloromethane
  9. dry with materialdried the organic layer over sodium sulphate
  10. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-5edade6785194286881e136a3cd643b3
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

Loading…