(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol → 3,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehyde

HRID 913315

Reaktionsgleichung

Reaktionsgleichung von HRID 913315
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:18][OH:19])[CH:7]=[C:8]([O:15][CH2:16][CH3:17])[C:9]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH3:2]>C1(C)C=CC=CC=1.O=[Mn]=O>[CH2:16]([O:15][C:8]1[CH:7]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH:18]=[O:19])[CH3:17]

Komponenten

4

Edukt 1

HCID 66912179(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol

Produkt 1

HCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 3,5-diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester (1.51 g, 4.98 mmol, 1.0 equiv) in toluene (5 mL) was added slowly over a time period of 15 min under slight cooling to 20° C. a solution of diisobutylaluminum hydride (8.9 mL, 12.45 mmol, 2.5 equiv; 20% solution in toluene). After 1 h, the excess of hydride was quenched by cautious addition of water (10 mL) and a 28% solution of NaOH (2 mL). The mixture was stirred for 30 min and the organic phase filtered over Hyflo Super Cel. The aqueous layer was extracted with toluene (2×50 mL), the combined organic phases washed with a sat. solution of NaCl (2×50 mL) and concentrated by evaporation under reduced pressure to afford 1.30 g (100%) of (3,5-diethoxy-4-pyrrol-1-yl-phenyl)-methanol. The crude alcohol (1.30 g, 4.98 mmol, 1.0 equiv) was dissolved in toluene (20 mL), and activated MnO2 (7.79 g, 89.5 mmol, 18.0 equiv) was added. The reaction mixture was heated to reflux for 7 h, after which time the reaction mixture was filtered through Hyflo Super Cel and concentrated yielding 1.15 g (89% yield) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.17 (t, J=7.0 Hz, 6H), 4.02 (q, J=7.0 Hz, 4H), 6.08-6.09 (m, 2H), 6.75-6.76 (m, 2H), 7.25 (s, 2H), 9.89 (s, 1H). MS (ISP): 260.1 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 h
  3. filtrationafter which time the reaction mixture was filtered through Hyflo Super Cel
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9d2791d9228e42b59bbe226c07716f0b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026365B2

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