Benzaldehyde → 3-Hydroxy-4-methyl-2-[(3-methyl-1H-indol-2-yl)-phenyl-methyl]-4-p-tolyl-cyclobut-2-enone

HRID 646067Notes

Reaction equation

[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[CH2:4][C:3]1=[O:7].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1>>[OH:7][C:3]1[C:2]([CH3:1])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:5](=[O:6])[C:4]=1[CH:15]([C:25]1[NH:26][C:27]2[C:32]([C:24]=1[CH3:23])=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 6736Skatole

HCID 685819552-Methyl-2-p-tolyl-cyclobutane-1,3-dione

Product 1

HCID 250507053-Hydroxy-4-methyl-2-[(3-methyl-1H-indol-2-yl)-phenyl-methyl]-4-p-tolyl-cyclobut-2-enone

Procedure

Using general procedure C, 2-methyl-2-p-tolyl-cyclobutane-1,3-dione (from Example 4.1) was reacted with benzaldehyde and 3-methyl-1H-indole to give the title compound as a colorless solid. MS: 406.6 ([M−H]−).

Sources & evidence

ORD record: ord-56e8391aa53e486e9e8c92ba97fd8b73
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705034B2

Reaction notes

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