Formaldehyde → 3-(trifluoroacetyl)-1H-indole-1-ylmethanol
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[CH2:16]=[O:17]>C(N(CC)CC)C.CC(C)=O>[F:15][C:2]([F:1])([F:14])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:16][OH:17])[CH:6]=1)=[O:4]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
The mixture of 4.80 g of 3-(trifluoroacetyl)-1H-indole, 1.35 g of paraformaldehyde and 0.10 g of triethylamine was stirred at 130° C. for 2 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, and hexane was added to the residue, as a result, a crystal was formed. The crystal was collected to obtain 5.36 g of 3-(trifluoroacetyl)-1H-indole-1-ylmethanol.
Workup
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- additionwas added to the residue, as a result
- customa crystal was formed
- customThe crystal was collected
Sources & evidence
- ORD record
- ord-c0833845bd4d4bfc98159442bc2ddafb
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541374B2
Reaction notes
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