Butanal → HCID 12411552, compound

HRID 1417497Notes

Reaction equation

HRID 1417497 reaction equation
[CH:1](=O)[CH2:2][CH2:3]C.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.C[C:16]1([CH3:24])[O:23][C:21](=[O:22])[CH2:20][C:18](=O)O1>C(#N)C.N1CCC[C@H]1C(O)=O>[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:18]([CH2:1][CH2:2][CH3:3])[CH2:20][C:21]([O:23][CH2:16][CH3:24])=[O:22])=[CH:7]1

Participants

6

Reactant 3

HCID 261ButanalHCID 798IndoleHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 12411552HCID 12411552, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 145742L-ProlineCatalystHCID 6342AcetonitrileSolvent

Procedure

10.7 g (148 mmol) of butanal was added gradually to 300 ml of a solution of 11.6 g of indole (98.6 mmol) and 14.2 g of Meldrum's acid (98.6 mmol) in acetonitrile at room temperature. 500 mg of proline was added to the reaction mixture which was then stirred overnight. The solvent was removed by evaporation under reduced pressure. The residue was dissolved in 200 ml of pyridine, and 15 ml of ethanol and 2.5 g of copper powder were added to the resulting solution. The reaction mixture was then refluxed for 4 hours and the copper powder was filtered off after this time. The solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 15% v/v solution of ethyl acetate in hexane) to yield 20.1 g (78%) of the title compound as an oil.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in 200 ml of pyridine
  3. addition15 ml of ethanol and 2.5 g of copper powder were added to the resulting solution
  4. temperatureThe reaction mixture was then refluxed for 4 hours
  5. filtrationthe copper powder was filtered off after this time
  6. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2d81e3d2f81041b7bc06d220836ea775
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

Loading…