Quinoline → HCID 66685333, compound

HRID 922281Notes

Reaction equation

HRID 922281 reaction equation
N1C2C(=CC=CC=2)C=CC=1.C([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:31]#[C:32][CH3:33])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([CH:25]([CH2:31][CH2:32][CH3:33])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 66685751HCID 66685751, compound

Product 1

HCID 66685333HCID 66685333, compoundYield 76.38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a 500 mL parr hydrogenater flask with ethyl acetate (5 mL) and quinoline (0.117 g, 1.4 mmol), was added methyl 3-[4-(benzyloxy)phenyl]hex-4-ynoate (0.2 g, 65.0 mmol) and 10% Pd/C (0.015 g) under N2 atmosphere. The RM was hydrogenated for 2 h. The RM was diluted with ethyl acetate (10 mL), filtered the catalyst through celite and evaporated to dryness under reduced pressure. The crude was purified by flash column chromatography on silica gel (100/200 mesh), to give the product (0.11 g, yield: 76.38%).

Workup

  1. filtrationfiltered the catalyst through celite
  2. customevaporated to dryness under reduced pressure
  3. customThe crude was purified by flash column chromatography on silica gel (100/200 mesh)

Sources & evidence

ORD record
ord-245a366d16144f599120ea507a9ce18e
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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