Benzothiophene 1,1-dioxide → 2,3-Dihydro-1lambda6-benzothiophene-1,1-dione

HRID 546254Notes

Reaction equation

HRID 546254 reaction equation
[S:1]1(=[O:11])(=[O:10])[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[H][H]>[Pd].C(O)C>[S:1]1(=[O:10])(=[O:11])[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 2

HCID 69997Benzothiophene 1,1-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 2844232,3-Dihydro-1lambda6-benzothiophene-1,1-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed benzo[b]thiophene 1,1-dioxide (5.0 g, 30.08 mmol), palladium on activated carbon (500 mg) and ethanol (100 mL). The bottle was placed on a Parr shaker and charged with 50 psi of hydrogen for 1 h. The reaction mixture was removed from the Parr shaker and filtered through a plug of celite and concentrated in vacuo to afford 2,3-dihydro-benzo[b]thiophene 1,1-dioxide (5.06 g, 100%) as a white solid.

Workup

  1. customThe reaction mixture was removed from the Parr shaker
  2. filtrationfiltered through a plug of celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40ce3701cd184f03b0d820fbf2c339ff
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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