m-Chloroperbenzoic acid → HCID 23043076, compound

HRID 2165585Notes

Reaction equation

HRID 2165585 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][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]([CH3:28])=[O:27])[CH:12]=3)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:30]=[CH:29][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]([CH3:28])(=[O:39])=[O:27])[CH:12]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23043063HCID 23043063, compound

Product 1

HCID 23043076HCID 23043076, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 439 mg of ethyl 9-p-chlorobenzyl-6-methylsulfinyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate from Example 24, in 10 cc of methylene chloride was added 353 mg of m-chloro perbenzoic acid. The resulting mixture was stirred for 18 hours at room temperature. The reaction mixture was diluted with ether and washed consecutively 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 30% hexane/ethyl acetate and yielded 200 mg (42%) of the pure title compound.

Workup

  1. washwashed consecutively 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 30% hexane/ethyl acetate

Sources & evidence

ORD record
ord-22c02351430c4407b2a127f12f20a2e8
Source dataset
uspto-grants-1990_07
Patent number
US04940719

Reaction notes

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