Potassium Hydroxide → HCID 19899097, compound

HRID 1196676Notes

Reaction equation

HRID 1196676 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][C:15]([CH3:22])([C:18]([O:20]C)=[O:19])[CH2:16][CH2:17][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][C:15]([CH3:22])([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19899024HCID 19899024, compound

Product 1

HCID 19899097HCID 19899097, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

1 g (3.12 mmol) of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-cyclohept[d]isoxazole-6-carboxylate was dissolved in 60 ml of methanol and a solution of 0.8 g of potassium hydroxide in 4 ml of water was added. The mixture was stirred at 20° C. for 48 hours and then at 50° C. for 6 hours. The methanol was removed by evaporation. Water was added and the mixture was acidified with 2N hydrochloric acid. The mixture was extracted three times with diethyl ether and the extracts were washed with sodium chloride solution and dried over magnesium sulfate. Evaporation and crystallization of the residue from ethyl acetate/hexane gave 0.594 g of 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-cyclohept[d]isoxazole-6-carboxylic acid of melting point 163° C.

Workup

  1. waitat 50° C. for 6 hours
  2. customThe methanol was removed by evaporation
  3. additionWater was added
  4. extractionThe mixture was extracted three times with diethyl ether
  5. washthe extracts were washed with sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation and crystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-707d890fbddd47e6a809ca6e7fcb16d8
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

Loading…