m-Chloroperbenzoic acid → HCID 23043063, compound

HRID 2165584Notes

Reaction equation

HRID 2165584 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:19]3[CH:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16][CH2:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[C:11]([S:26][CH3:27])[CH:12]=3)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19]3[CH:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16][CH2:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[C:11]([S:26]([CH3:27])=[O:38])[CH:12]=3)=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 17913401HCID 17913401, compound

Product 1

HCID 23043063HCID 23043063, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 498 mg of ethyl 9-p-chlorobenzyl-6-methylthio-1,2,3,4-tetrahydrocarbazol-1-yl-acetate from Example 23 in 10 cc of methylene chloride was added 300 mg of m-chloro perbenzoic acid. The resulting mixture was stirred for 1.5 hours at room temperature. The reaction mixture was diluted with ether and consecutively washed with a solution of sodium bicarbonate, water and brine. The crude product obtained after evaporation of the organic layer was purified on silica gel by flash chromatography eluting with 20% hexane/ethyl acetate and yielded 420 mg (82%) of the pure title compound.

Workup

  1. washconsecutively washed with a solution of sodium bicarbonate, water and brine
  2. customThe crude product obtained
  3. customafter evaporation of the organic layer
  4. customwas purified on silica gel by flash chromatography
  5. washeluting with 20% hexane/ethyl acetate

Sources & evidence

ORD record
ord-2aa9637f54744098a16f97f7b50096e3
Source dataset
uspto-grants-1990_07
Patent number
US04940719

Reaction notes

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