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

HRID 1614205Notes

Reaction equation

HRID 1614205 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:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1CCC[C@H]1C(O)=O.C(#N)C>[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH:15]([CH:20]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13](=[O:14])[O:12]1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 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-Yield 67.3%

Reagents, catalysts & solvents 2

HCID 145742L-ProlineCatalystHCID 6342AcetonitrileSolvent

Procedure

Indole (10 g, 85 mmol), Meldrum's acid (12.3 g, 85 mmol), benzaldehyde (18.11 g, 171 mmol) and proline (0.05 g) were combined with 50 ml of acetonitrile and stirred in an oil bath at approximately 35°-40° C. for two hours [Y. Oikawa, H. Hirasawa, and O. Honemitsu, Tetrahedron Letters, 1759 (1978)]. The reaction mixture was concentrated in vacuo to dryness. The residue was slurried with methanol and filtered to provide 19.99 grams of 3-[α-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)benzyl]indole. A portion of the product was recrystallized from ethyl acetate to provide a white crystalline product: mp 147°-150° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. filtrationfiltered

Sources & evidence

ORD record
ord-48211fddcfd742d38dde67a0823242bd
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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