Benzaldehyde → 1,3-Dioxane-4,6-dione, 5-(1H-indol-3-ylphenylmethyl)-2,2-dimethyl-

HRID 250188Notes

Reaction equation

HRID 250188 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:10][C:11]1([CH3:19])[O:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[O:12]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1CCCC1C(O)=O>C(#N)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]2[C:15](=[O:17])[O:16][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:18])=[CH:2]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 614proline dl-formHCID 798IndoleHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 111318571,3-Dioxane-4,6-dione, 5-(1H-indol-3-ylphenylmethyl)-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described in Tetrahedron 56 (2000) 5479-5492, indole (5.0 g, 42.7 mmole) and 2,2-dimethyl-[1,3]dioxane-4,6-dione (6.15 g, 42.7 mmole) were mixed in acetonitrile (50 ml). To this mixture was added benzaldehyde (9.06 g, 85.4 mmole) and d,l-proline (0.25 g). The mixture was stirred at room temperature for 18 hours after which time much of the reaction mixture had turned solid. The solvent was evaporated at reduced pressure and the residue was triturated with ether and filtered. The filter cake was washed with several portions of ether to afford pure 5-[(1H-indol-3-yl)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione, 11.83 g, as a light pink solid (MS (M−H)=348) which was used without further purification in the next step.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. customthe residue was triturated with ether
  3. filtrationfiltered
  4. washThe filter cake was washed with several portions of ether

Sources & evidence

ORD record
ord-c9aa7804b66047968f54e9a4d217021e
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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