Ethanol → HCID 25006856, compound

HRID 383245Notes

Reaction equation

[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH2:7][O:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11](O)[CH:10]=3)=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[CH3:27])[NH2:23].[CH2:28]=[O:29].[CH2:30](O)C>>[CH3:19][C:20]1[CH:21]=[C:22]([N:23]2[CH2:30][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][C:11]=3[O:29][CH2:28]2)[O:8][CH2:7][C:6]([C:5]2[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:15]4)[CH:24]=[CH:25][C:26]=1[CH3:27]

Participants

Reactant 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 72483,4-Dimethylaniline

HCID 219100Phenoxodiol

Product 1

HCID 25006856HCID 25006856, compoundYield 21%

Procedure

4′,7-Dihydroxyisoflav-3-ene (500 mg, 2.08 mmol) was dissolved in absolute ethanol (10 mL). 3,4-Dimethylaniline (293 mg, 2.08 mmol) was added followed by formaldehyde (6 mL, 0.09 mmol, 37 wt. %). The reaction was stirred for a day at room temperature. The light pink precipitate was collected to afford the title compound (166 mg, 21%).

Workup

customThe light pink precipitate was collected

Sources & evidence

ORD record: ord-6feb6b4d755343db8ac7b2a3432611a2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367659B2

Reaction notes

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