Acetic Acid → HCID 19899067, compound

HRID 1196652Notes

Reaction equation

HRID 1196652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]3[CH2:13][CH2:14][CH:15]([C:18]([O-:20])=[O:19])[CH2:16][CH2:17][CH:11]3[O:10][N:9]=2)=[CH:4][CH:3]=1.[C:21](O)(=O)C>S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][CH2:14][CH:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86745847HCID 86745847, compound

Product 1

HCID 19899067HCID 19899067, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

5.3 g (0.053 mol) of chromium trioxide were added to a solution of 6.14 g (0.02 mol) of methyl 3-(4-chlorophenyl-3a,5,6,7,8,8a-hexahydro-4H-cyclohept[d]isoxazole-6-carboxylate (mixture of two diastereoisomers, prepared as described in the last paragraph of Example 1) in 110 ml of acetic acid and 0.5 ml of concentrated sulfuric acid. The mixture was heated to 90° C. for 40 minutes. Excess acetic acid was removed by evaporation, water and 2N sodium carbonate solution were added and the mixture was extracted with diethyl ether. Purification by column chromatography on silica gel using diethyl ether/hexane (1:1) for the elution gave 2.57 g or pure methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]-isoxazole-6-carboxylate of melting point 70°-71° C.

Workup

  1. additionmixture of two diastereoisomers
  2. customprepared
  3. customExcess acetic acid was removed by evaporation, water and 2N sodium carbonate solution
  4. additionwere added
  5. extractionthe mixture was extracted with diethyl ether
  6. customPurification by column chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-9df54423ae8148e18b1a5849c414c513
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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