Water → HCID 14128057, compound

HRID 414346Notes

Reaction equation

HRID 414346 reaction equation
[CH2:1]([C:4]1[C:12]2[O:11][N:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:8]=2[CH:7]=[C:6]([Cl:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:30])C=1.O.[OH-].[Na+]>C(Cl)Cl>[Cl:20][C:6]1[C:5]2[O:21][CH:2]([CH2:3][OH:30])[CH2:1][C:4]=2[C:12]2[O:11][N:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 135583512HCID 135583512, compound

Product 1

HCID 14128057HCID 14128057, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice-cooled solution of 7-allyl-5-chloro-3-(2-fluorophenyl)-6-hydroxy-1,2-benzisoxazole (9.5 g) in methylene chloride (200 ml), m-chloroperbenzoic acid (16.4 g) was added in small portions under agitaiton, and the solution was subsequently refluxed for 3 hours. After cooling the solution, water and 100 ml of 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, 6.5 g of 5-chloro-7,8-dihydro-3-(2-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-methanol was obtained. m.p. 136°-139° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 319.

Workup

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

Sources & evidence

ORD record
ord-57c1bb46ca5b468bbd3e88f14c6958c1
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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