6-Methoxy-2-(1-cyclohexenyl)benzo[b]thiophene → 6-Methoxy-2-cyclohexylbenzo[b]thiophene

HRID 354082Notes

Reaction equation

HRID 354082 reaction equation
[C:1]1([C:7]2[S:11][C:10]3[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>[Pd].C(OCC)(=O)C>[CH:1]1([C:7]2[S:11][C:10]3[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 235129036-Methoxy-2-(1-cyclohexenyl)benzo[b]thiophene

Product 1

HCID 108794206-Methoxy-2-cyclohexylbenzo[b]thiopheneYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 19, Step 1 (264 mg) and 10% Palladium on Carbon (60 mg) in 30 mL of ethyl acetate was added to a Parr shaker flask and hydrogenated at 50 psi for 16 hrs. at room temperature. The mixture was filtered over celite and concentrated. The crude product was chromatographed on silica gel using Hexanes as the eluant to give 210 mg of the title compound.

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered over celite and
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-2c077a95b394429ebdf2ebb1d871f618
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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