Water → HCID 19899066, compound
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH2:15][CH2:16][CH:17]([C:20]([O:22]C)=[O:21])[CH2:18][CH2:19][C:13]=3[O:12][N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[K+].O>CO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]3[CH2:15][CH2:16][CH:17]([C:20]([OH:22])=[O:21])[CH2:18][CH2:19][C:13]=3[O:12][N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
0.286 g (0.00091 mol) of methyl 5,6,7,8-tetrahydro-3-(4-isopropylphenyl)-4H-cyclohept[d]isoxazole-6-carboxylate was dissolved in 15 ml of methanol, 0.15 g (0.0027 mol) of potassium hydroxide and 2 ml of water were added and the mixture was stirred at 20° C. for 68 hours. The methanol was removed by evaporation. Water was added and the mixture was extracted once with diethyl ether. The aqueous layer was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with sodium chloride solution and dried over magnesium sulfate. Evaporation gave a residue which was crystallized from methylcyclohexane to give 200 mg of 5,6,7,8-tetrahydro-3-(4-isopropylphenyl)-4H-cyclohept[d]isoxazole-6-carboxylic acid of melting point 109°-111° C.
Workup
- customThe methanol was removed by evaporation
- additionWater was added
- extractionthe mixture was extracted once with diethyl ether
- extractionextracted with ethyl acetate
- washThe extract was washed with sodium chloride solution
- dry with materialdried over magnesium sulfate
- customEvaporation
- customgave a residue which
- customwas crystallized from methylcyclohexane
Sources & evidence
- ORD record
- ord-6e88b182f22f47c5a95d5756fa26d24b
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05114960
Reaction notes
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