HCID 118113146, compound → HCID 118113383, compound

HRID 1485064Notes

Reaction equation

HRID 1485064 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]1([CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([CH:10]=[O:11])=[CH:12][CH:13]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 118113146HCID 118113146, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 118113383HCID 118113383, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution in ethyl acetate (22.0 mL) of the compound (1.79 g) obtained in step (1) above, 10% palladium/carbon (179 mg) was added. The mixture was stirred at room temperature for 22 hours in a hydrogen atmosphere. More of 10% palladium/carbon (179 mg) was added and the mixture was stirred at room temperature for 3 hours in a hydrogen atmosphere. The insoluble matter was removed by filtration through Celite (registered trademark). After concentrating the filtrate under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30) to give the titled compound as a crude product (1.23 g).

Workup

  1. customThe insoluble matter was removed by filtration through Celite (registered trademark)
  2. concentrationAfter concentrating the filtrate under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30)

Sources & evidence

ORD record
ord-8bc2b71c832446c18b8e84db48dcd378
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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