Formaldehyde → HCID 23149195, compound

HRID 1983050Notes

Reaction equation

HRID 1983050 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].[CH2:12]=[O:13].C(N(CC)CC)C>CC(C)=O>[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][OH:13])[CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 10256Indole-3-Carboxaldehyde

Product 1

HCID 23149195HCID 23149195, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 5.81 g of 3-formyl-1H-indole, 1.80 g of paraformaldehyde and 0.40 g of triethylamine was stirred at 120 ° C. for 3 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered, and then the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.08 g of 3-formyl-1H-indole-1-ylmethanol.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-638ca220a06b4133ab56c62d16e8c4d1
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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