Formaldehyde → HCID 19773187, compound

HRID 1614198Notes

Reaction equation

HRID 1614198 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[CH2:12]=O.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.O>C(#N)C.CC(C)=O.N1CCC[C@H]1C(O)=O>[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH:19]([CH2:12][C:7]2[NH:8][C:9]3[C:5]([CH:6]=2)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:17](=[O:18])[O:16]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 138725-MethoxyindoleHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 19773187HCID 19773187, compound

Reagents, catalysts & solvents 3

HCID 145742L-ProlineCatalystHCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 5-methoxyindole (10.0 g, 67.9 mmol), 5.5 ml formaldehyde (37% aqueous solution), Meldrum's acid (10 g, 69 mmol), and proline (0.4 g) in 40 ml of acetonitrile was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo to provide a brown foam. The product was taken up in about 50 ml of acetone, and about 50 ml of water was added to the cloud point. The mixture was allowed to stand in the freezer and, after crystallization began, additional water was added with swirling again to the cloud point. Vacuum-assisted filtration provided 16.2 g of 2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)methyl-5-methoxyindole as sand-colored crystals.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto provide a brown foam
  3. customafter crystallization
  4. additionadditional water was added
  5. filtrationVacuum-assisted filtration

Sources & evidence

ORD record
ord-93d807f30a374b4dac02697bfb7b6585
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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