Acetaldehyde → HCID 53965436, compound

HRID 566865Notes

Reaction equation

HRID 566865 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].Cl.[CH:20](=O)[CH3:21]>CO>[CH2:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1)[CH3:21]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53965436HCID 53965436, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5 g of ethyl 4-aminocinnamate in 100 ml of methanol, 0.1 ml of acetaldehyde, 1.256 g of sodium cyanoborohydride and 2.15 ml of hydrochloric acid 23% were added. The solution was stirred at room temperature for one day, then the solvent evaporated in vacuum and the crude residue purified by flash chromatography (n-exane/ethyl acetate 9/1) to yield 2.1 g of intermediate as a yellow solid.

Workup

  1. customthe solvent evaporated in vacuum
  2. customthe crude residue purified by flash chromatography (n-exane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-0d5f62ffa6dc4191afbc8652937f1129
Source dataset
uspto-grants-2001_01
Patent number
US06177408B1

Reaction notes

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