Ethanol → HCID 25002237, compound

HRID 383234Notes

Reaction equation

HRID 383234 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]1[CH2:6]O[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10](O)[CH:9]=2.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:27]=[O:28].[OH2:29].[CH2:30](O)C>>[CH2:19]([N:26]1[CH2:30][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][C:10]=2[O:28][CH2:27]1)[O:29][CH2:6][C:5]([C:4]1[CH:3]=[C:2]([OH:1])[CH:18]=[CH:17][CH:16]=1)=[CH:14]3)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 712FormaldehydeHCID 962WaterHCID 7504BenzylamineHCID 9813510HCID 9813510, compound

Product 1

HCID 25002237HCID 25002237, compound

Procedure

3′,7-Dihydroxyisoflav-3-ene (100 mg, 0.42 mmol) was dissolved in ethanol (4 ml). Benzylamine (0.14 ml, 1.28 mmol) was added followed by formaldehyde solution (0.42 ml, 5.59 mmol, 37% wt.). The reaction was stirred at room temperature for 1 day. Reaction mixture was poured into water (50 ml) then extracted with ethyl acetate (3×30 ml) and the combined organic layers reduced. The solid was flash chromatographed using 100% dichloromethane. Fractions 6-12 were combined and reduced to afford the title compound.

Workup

  1. customReaction mixture
  2. extractionthen extracted with ethyl acetate (3×30 ml)
  3. customchromatographed

Sources & evidence

ORD record
ord-0a73d515d71e4b24b09f8bc0019c1b5e
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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