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9th January 2013 @ 02:36

Reaction Scheme

Anisidine (891 mg, 7.24 mmol, 1.1 equiv.) and 2,5-hexanedione (0.77 mL, 6.58 mmol, 1 equiv.) were heated to 110 °C (oil bath temp.) for 4 hours; TLC indicated SM still present so RM stirred at 110 ˚C for 16 h. TLC indicated reaction complete so the crude black mixture was purified by flash column chromatography over silica (5–20% EtOAc in Petroleum Ether) to obtain the desired product (1.21 g, 6.01 mmol, 91% yield) as a pale yellow solid.

TLC:

AEW 36-1, 4 h.jpg
 
AEW 36-1.jpg

 

1H and 13C NMR:

Hazard and Risk Assessment:

As for: Repeat Preparation of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole (AEW 1-1) but using: 

Anisidine; risk class 2; HU and M; very toxic by inhalation, in contact with skin and if swallowed, danger of culmulative effects, may cause cancer and harmful to aquatic organisms.

InChI=1S/C13H15NO/c1-10-4-5-11(2)14(10)12-6-8-13(15-3)9-7-12/h4-9H,1-3H3

See Also:

Synthesis of 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole (AEW 35-1)

Synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)phenol (AEW 37-1)

Synthesis of 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonic acid (AEW 38-1)

Synthesis of 1-(benzo[d][1,3]dioxol-5-yl)-2,5-dimethyl-1H-pyrrole (AEW 39-1)

Synthesis of 2-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 40-1)

Synthesis of 3-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 41-1)

Synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 42-1)

Synthesis of 2-(2,5-dimethyl-1H-pyrrol-1-yl)pyrimidine (AEW 43-1)

Synthesis of 2,5-dimethyl-1-phenyl-1H-pyrrole (AEW 44-1)

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AEW 36-1.png
AEW 36-1.jpg
AEW 36-1, 4 h.jpg