Water → HCID 14128066, compound

HRID 414353Notes

Reaction equation

HRID 414353 reaction equation
[CH2:1]([C:4]1[C:12]2[O:11][N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:8]=2[CH:7]=[C:6]([Cl:21])[C:5]=1[OH:22])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:31])C=1.O.[OH-].[Na+]>C(Cl)Cl>[Cl:21][C:6]1[C:5]2[O:22][CH:2]([CH2:3][OH:31])[CH2:1][C:4]=2[C:12]2[O:11][N:10]=[C:9]([C:13]3[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[F:19])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 135583511HCID 135583511, compound

Product 1

HCID 14128066HCID 14128066, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice-cooled solution of 7-allyl-5-chloro-3-(2,6-difluorophenyl)-6-hydroxy-1,2-benzisoxazole (3.1 g) in methylene chloride (80 ml), 4.6 g of m-chloroperbenzoic acid was added in small portions under agitation, and the mixture was subsequently refluxed for 5 hours. After cooling the mixture, water and an aqueous solution of 2N sodium hydroxide were added and the mixture was subjected to extraction with methylene chloride. The methylene chloride layer was washed with water and dried. By distilling off the solvent, 2.8 g of 5-chloro-3-(2,6-difluorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-methanol was obtained. m.p. 166°-169° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 337.

Workup

  1. additionwas added in small portions under agitation
  2. temperaturethe mixture was subsequently refluxed for 5 hours
  3. extractionthe mixture was subjected to extraction with methylene chloride
  4. washThe methylene chloride layer was washed with water
  5. customdried
  6. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-bdb01b967d9845d49a38af8c69b0b8b0
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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