Acetone → HCID 14128067, compound

HRID 414354Notes

Reaction equation

HRID 414354 reaction equation
CC(C)=[O:3].[Cl:5][C:6]1[C:7]2[O:25][CH:24]([CH2:26][OH:27])[CH2:23][C:8]=2[C:9]2[O:13][N:12]=[C:11]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])[C:10]=2[CH:22]=1.S(=O)(=O)(O)O>[O-2].[Cr+6].[O-2].[O-2].O>[Cl:5][C:6]1[C:7]2[O:25][CH:24]([C:26]([OH:3])=[O:27])[CH2:23][C:8]=2[C:9]2[O:13][N:12]=[C:11]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])[C:10]=2[CH:22]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14128066HCID 14128066, compound

Product 1

HCID 14128067HCID 14128067, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To the stirred acetone (50 ml) solution of 2.8 g of the 5-chloro-3-(2,6-difluorophenyl)-7,8-dihydrofuro[2,3-g]1,2-benzisoxazole-7-methanol prepared in Example 20, a mixture of chromium (VI) oxide (3.0 g), water (7 ml) and concentrated sulfuric acid (4.2 g) was added dropwise over time, and the agitation was continued for 9 hours at room temperature. The insolubles were filtered off by suction and the acetone was distilled off. Water was added to the residue, and the solution was subjected to extraction with ether. The ether layer was washed with water and dried. After distilling off the solvent, the residue was recrystallized from acetone-water, yielding 1.0 g of 5-chloro-3-(2,6-difluorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 239.5°-241° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 351.

Workup

  1. additionwas added dropwise over time
  2. filtrationThe insolubles were filtered off by suction
  3. distillationthe acetone was distilled off
  4. additionWater was added to the residue
  5. extractionthe solution was subjected to extraction with ether
  6. washThe ether layer was washed with water
  7. customdried
  8. distillationAfter distilling off the solvent
  9. customthe residue was recrystallized from acetone-water

Sources & evidence

ORD record
ord-89be0210981445b885d1c307eacd468c
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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