3,4,5-Trimethoxyphenol → 2'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone

HRID 1095273

Reaktionsgleichung

Reaktionsgleichung von HRID 1095273
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[OH:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[C:4]=1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=1

Komponenten

3

Edukt 2

HCID 695053,4,5-TrimethoxyphenolHCID 3194633-(4-nitrophenyl)prop-2-enoyl Chloride

Produkt 1

HCID 727670692'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalconeAusbeute 22 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3,4,5-trimethoxyphenol (1.85 g, 10 mmol) and 4-nitrocinnamoyl chloride (2.11 g, 10 mmol) was dissolved in BF3-Et2O complex (10 ml) and heated to 80° C. for 10 min, and then quenched with excess of water. The aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated and the residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3) gave 7a (0.79 g, 22%) and 7b (1.54 g, 43%). 1H NMR (400 MHz, CDCl3) μ 3.81 (s, 3H), 3.90 (s, 3H), 3.91 (s, 3H), 6.29 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.76 (d, J=16.0 Hz, 1H), 8.01 (d, J=16.0 Hz, 1H), 8.26 (d, J=8.8 Hz, 2H), 13.44 (s, 1H).

Aufarbeitung

  1. dissolutionwas dissolved in BF3-Et2O complex (10 ml)
  2. customquenched with excess of water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. concentrationThe combined organic layer was concentrated
  5. customthe residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3)

Quellen und Nachweise

ORD-Eintrag
ord-4049c48a3e50449dade86f120b203cfc
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138165B2

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