Trifluoroacetic acid → (3R)-(-)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH:11](=[O:15])/[CH:12]=[CH:13]/[CH3:14].FC(F)(F)C(O)=O.C([C@@H]1N[C@H](C(C)(C)C)N(C)C1=O)C1C=CC=CC=1>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C@H:13]([CH3:14])[CH2:12][CH:11]=[O:15])=[CH:3]1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 117811-Methylindole

HCID 447466Crotonaldehyde

HCID 103098345-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone, (2S,5S)-

Product 1

HCID 9899133(3R)-(-)-3-(1-Methyl-1H-indol-3-yl)butyraldehyde

Procedure

This example describes the alkylation of 1-methyl-1H-indole with (E)-crotonaldehyde, catalyzed by the trifluoroacetic acid salt of (1), to provide (R)-3-(1-methyl-1H-indol-3-yl)-butanal.

Sources & evidence

ORD record: ord-b5aa7e2cdb164ca98980660796a5ba7a
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784323B2

Reaction notes

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