m-Chloroperbenzoic acid → HCID 13746693, compound

HRID 1731629Notes

Reaction equation

HRID 1731629 reaction equation
[CH2:1]1[C:22]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=[CH:16][C:10]=4[CH2:9][CH2:8][C:7]=3[CH:21]=2)[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:31])C=1.[OH-].[Ca+2].[OH-]>C(Cl)Cl>[CH2:1]1[C:22]2[C:4](=[CH:5][C:6]3[S:12](=[O:31])[C:11]4[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=[CH:16][C:10]=4[CH2:9][CH2:8][C:7]=3[CH:21]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 13746692HCID 13746692, compound

Product 1

HCID 13746693HCID 13746693, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2,3,10,11-tetrahydro1H-benzo[b]indeno[5,6-f]thiepin-7-carboxylate (3.05 g; 9.84 mmole) in methylene chloride (200 ml) stirred in a cooling bath at 0°-5° C. was added 85% m-chloroperbenzoic acid (2.00 g; 9.85 mmole) in small portions during 1 hour. After stirring the reaction mixture for 30 minutes at room temperature, more methylene chloride was added to get a clear solution and then calcium hydroxide (4 g) was added. The suspension was stirred for 25 minutes, filtered and evaporated. The crude product was purified by column chromatography (Merck silica gel eluted with 1:4 ethyl acetate/toluene) to yield 2.121 g (66%) of the title compound, m.p. 150°-154° C. (from MeCN).

Workup

  1. customto get a clear solution
  2. stirringThe suspension was stirred for 25 minutes
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by column chromatography (Merck silica gel eluted with 1:4 ethyl acetate/toluene)

Sources & evidence

ORD record
ord-c168a6cd9e124fa2a809c1df7b8b95f2
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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