Sodium Carbonate → 2-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan

HRID 2059636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059636
I[C:2]1([O:9][CH3:10])[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH2:3]1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]#[C:17][C:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)=[O:19].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[O:8][C:6]2[CH:7]=[C:2]([O:9][CH3:10])[CH:3]=[CH:4][C:5]=2[C:17]=1[C:18](=[O:19])[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 574219633-(2-Furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-oneHCID 687733295-Iodo-5-methoxyphenol

Produkt 1

HCID 115605482-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furanAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
102.5 °C

Versuchsvorschrift

5-Iodo-5-methoxyphenol (125 mg, 0.5 mmol), 3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)-prop-2-yn-1-one (172 mg, 0.6 mmol), LiCl (21.2 mg, 0.5 mmol) and Na2CO3 (265 mg, 2.5 mmol) were added to anhydrous DMF (3 ml) and flushed with N2 three times. Pd(OAc)2 was added to the reaction mixture and again flushed with N2. The reaction mixture was heated to 100-105° C. for 6 h and then reaction was cooled to room temp. Quenched by addition of aqueous NH4Cl solution and extracted with EtOAc. 2-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan was isolated in 12% yield by silica gel column chromatography using 20 to 40% EtOAc in hexane. 1H NMR (300 MHz, CDCl3) δ: 3.75(s, 6H, OMe), 3.86(s, 3H, OMe), 3.90(s, 3H, OMe), 6.44-6.46(m, 1H), 6.87(dd, J=2.1, 8.7, 1H), 6.97(d, J=3.6, 1H), 7.07(d, J=2.1, 1H), 7.15(s, 2H), 7.36(d, J=8.7, 1H), 7.41(d, J=1.2, 1H). MS (ES) m/z: 408.9(M+H)+.

Aufarbeitung

  1. customflushed with N2 three times
  2. additionPd(OAc)2 was added to the reaction mixture
  3. customagain flushed with N2
  4. customreaction
  5. temperaturewas cooled to room temp
  6. customQuenched by addition of aqueous NH4Cl solution
  7. extractionextracted with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3d2bc53a70ff47aaad9791e50b3ebc3d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278290B2

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