Isoxanthohumol → Sophoraflavanone B

HRID 564215

Reaction equation

HRID 564215 reaction equation
[CH3:1][C:2]([CH3:26])=[CH:3][CH2:4][C:5]1[C:6]([OH:25])=[CH:7][C:8]([O:23]C)=[C:9]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[O:11][C:10]=12>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3].C1COCC1>[CH3:1][C:2]([CH3:26])=[CH:3][CH2:4][C:5]1[C:10]2[O:11][C@H:12]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[CH2:13][C:14](=[O:15])[C:9]=2[C:8]([OH:23])=[CH:7][C:6]=1[OH:25]

Participants

4

Reactant 1

HCID 513197Isoxanthohumol

Product 1

HCID 480764Sophoraflavanone BYield 92.3%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of isoxanthohumol (50 mg, 0.14 mmol), KI (34 mg, 0.21 mmol) and Sc(OTf)3 (105 mg, 0.21 mmol), 10 ml of THF are added and the solution is heated for 2.5 h under reflux. The mixture is stirred overnight at room temperature and concentrated in vacuum. The scandium salt is separated off via a short silica gel column (eluted with CHCl3/methanol=100:1). The resultant solution is concentrated to dryness in vacuum, the residue is taken up in CHCl3 and eluted through a silica gel column using CHCl3/-methanol=100:1. 8-Prenylnaringenin (formula (III) where R1=prenyl, R2=H) (44 mg, 92%) is obtained as a light-yellowish solid.

Workup

  1. additionare added
  2. temperaturethe solution is heated for 2.5 h
  3. temperatureunder reflux
  4. concentrationconcentrated in vacuum
  5. customThe scandium salt is separated off via a short silica gel column (eluted with CHCl3/methanol=100:1)
  6. concentrationThe resultant solution is concentrated to dryness in vacuum
  7. washeluted through a silica gel column

Sources & evidence

ORD record
ord-4784225c6fc94740bca3df471d39b4d1
Source dataset
uspto-grants-2011_11
Patent number
US08067622B2

Linked notes

Loading…