Potassium Carbonate → Ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoate

HRID 568712Notes

Reaction equation

HRID 568712 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:25]([CH2:31][CH2:32][CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>CC(CC)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH:25]([CH2:31][CH2:32][CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79071Ethyl 2-bromovalerateHCID 1355896553-(4-Chloro-phenyl)-benzo[D]isoxazol-6-OL

Product 1

HCID 14012537Ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 6 g of 3-(4-chloropheyl)-6-hydroxy-1,2-benzisoxazole, 10.2 g of potassium carbonate, 5.12 g of ethyl 2-bromovalerate and 100 ml of methylethyl ketone is stirred under reflux for 3 hr. The reaction mixture is poured into 1 liter of ice/dil hydrochloric acid and the precipitate is collected and dried. Recrystallization from ether gives ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoate, mp 88° C.

Workup

  1. temperatureunder reflux for 3 hr
  2. customthe precipitate is collected
  3. customdried
  4. customRecrystallization from ether

Sources & evidence

ORD record
ord-9ae0def2dfd64fe5a465344c4caacdff
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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