3-Thiophenecarboxaldehyde → HCID 10013061, compound

HRID 1992315Notes

Reaction equation

HRID 1992315 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH2:12]>C(O)C.[Pd]>[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH:12][CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

5

Reactant 2

HCID 681353-ThiophenecarboxaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10013061HCID 10013061, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 3-thiophenecarboxaldehyde (8.75 mL) cooled to 0° C. was added aminoacetaldehyde dimethylacetal (14.2 mL). The clear solution was stirred at room temperature for 60 h. The solution was diluted with ethanol and hydrogenated at 56 psi in the presence of 10% Pd/C (5 g) overnight. The catalyst was filtered off and washed with MeOH. The solvent was removed by rotary evaporation and co-evaporated with toluene to afford an oil (19 g, 94% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. customThe solvent was removed by rotary evaporation and co-evaporated with toluene

Sources & evidence

ORD record
ord-ba3a5c97badd49ee999bc90cda033621
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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