Formaldehyde → HCID 19773187, compound

HRID 1461356Notes

Reaction equation

HRID 1461356 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. filtrationwith swirling again to the cloud point Vacuum-assisted filtration

Sources & evidence

ORD record
ord-48807729b3524767b30fdce693f83a4d
Source dataset
uspto-grants-1991_12
Patent number
US05075313

Reaction notes

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