Ethanol → 6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalene-1-carbonitrile

HRID 2242603Notes

Reaction equation

HRID 2242603 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]#[N:21])=[CH:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO.[H][H]>[Pd].C(O)(=O)C>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([C:20]#[N:21])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 590217566-Benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 590217496-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalene-1-carbonitrileYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-Benzenesulfonyl-3,4-dihydro-naphthalene-1-carbonitrile (5.1 g, 17.2 mmol), 70 mL EtOH, and 50 mL acetic acid were placed in a Parr vessel, and 1.0 g of 10% Palladium on carbon (Fluka Chemica Co.) was added. The reaction mixture was shaken for 15 hours under 55 psi hydrogen. The Parr vessel was purged with nitrogen and the reaction mixture was filtered. The filtrate was added to 500 mL water, and the aqueous mixture was extracted twice with 200 mL of EtOAc. The combined organic layers were dried (MgSO4) and evaporated to yield 4.6 g (15.5 mmol, 90%) of 6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalene-1-carbonitrile as an oil. MS: 298 (M+H)+.

Workup

  1. additionwas added
  2. customThe Parr vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. additionThe filtrate was added to 500 mL water
  5. extractionthe aqueous mixture was extracted twice with 200 mL of EtOAc
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-c122a5c2cc6b4de4ada5246f4153650e
Source dataset
uspto-grants-2010_03
Patent number
US07671235B2

Reaction notes

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