HCID 2888318, compound → Loureirin A

HRID 1603168Notes

Reaction equation

HRID 1603168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:14]>C(O)C.[Pt]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)=[O:14]

Participants

4

Reactant 1

HCID 2888318HCID 2888318, compound

Product 1

HCID 5319081Loureirin AYield 25.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 568 mg (2 mmol) of 2,4dimethoxy-4'-hydroxychalcone in ethanol (20 ml) was added 50 mg of platinum on charcoal (10%) and hydrogenated at 20 atm for 18 h. The colourless solution was filtered and concentrated in vacuo to give 606 mg, from which 143.7 mg (24%) of 3-(2,4-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-on was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 60 g) using petroleum ether-ethyl acetate (4:1, 500 ml, 3:1, 500 ml) as eluents, m.p. 126.4-127.4° C.

Workup

  1. filtrationThe colourless solution was filtered
  2. concentrationconcentrated in vacuo
  3. customto give 606 mg

Sources & evidence

ORD record
ord-74dc60c4c1c747c882eacacff380c34c
Source dataset
uspto-grants-1999_11
Patent number
US05985935

Reaction notes

Loading…