Ethanol → HCID 67232883, compound

HRID 1465939Notes

Reaction equation

HRID 1465939 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2].C(O)C>[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 67233056HCID 67233056, compound

Product 1

HCID 67232883HCID 67232883, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-hydroxy-2-styryl-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (example 21.g, 0.44 mmol) and 10% palladium on carbon (100 mg) in 20 mL of 1:1 ethyl acetate:ethyl alcohol was placed under a hydrogen atmosphere at 19 PSI on a parr shaker. At 7 hours an additional 60 mg of 10% Pd/C was added, after 24 hours an additional 75 mg of 10% Pd/C was added, and the reaction was stopped at 29 hours. The mixture was filtered through a celite pad and purified by flash chromatography, eluting the desired product from silica gel with a gradient of 20-80% ethyl acetate in hexanes to give 77 mg of desired product: MS: (+) m/z 327.9 (M+1)

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through a celite pad
  3. custompurified by flash chromatography
  4. washeluting the desired product from silica gel with a gradient of 20-80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-16f713902fe64d0c99d919bdd4227267
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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