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

HRID 547939Notes

Reaction equation

HRID 547939 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

HCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeYield 89.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

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 diisobutylaluminium hydride (8.9 mL, 12.45 mmol, 2.5 equiv; 20% solution in toluene). After 1 h the excess 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]+.

Workup

  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

Sources & evidence

ORD record
ord-da75adf934234bff91c981524556ecce
Source dataset
uspto-grants-2011_05
Patent number
US07939661B2

Reaction notes

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