2,5-DIMETHYL-1-PHENYLPYRROLE-3-CARBOXALDEHYDE synthesis
- Product Name:2,5-DIMETHYL-1-PHENYLPYRROLE-3-CARBOXALDEHYDE
- CAS Number:83-18-1
- Molecular formula:C13H13NO
- Molecular Weight:199.25
83-24-9
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83-18-1
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Yield: 29%
Reaction Conditions:
Stage #1:2,5-dimethyl-1-phenyl-1H-pyrrole with N,N-dimethyl-formamide;trichlorophosphate in toluene at 80; for 3 h;
Stage #2: with water;sodium carbonate in toluene at 20;Product distribution / selectivity;
Steps:
1.5
Preparation of 2,5-Dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (5) To a well stirred solution of 2,5-dimethyl-1-phenyl-1H-pyrrole (7.65 g, 44.7 mmol) and DMF (3.6 g, 49.2 mmol) in 70 mL of dry toluene, phosphorus oxychloride (6.9 g, 44.7 mmol) was added in small portions. The mixture was heated to 80° C. for 3 hrs. The solution was allowed to cool to room temperature, then 100 mL of saturated aqueous Na2CO3 was added. The aqueous layer was extracted with EtOAc (100 mL*3). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane:EtOAc=10:1) to give 2.6 g of 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (29%). MS [M++1]=200, LC-MS: tR=1.96 mm.
References:
REGENTS OF THE UNIVERSITY OF CALIFORNIA US2008/293766, 2008, A1 Location in patent:Page/Page column 10
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83-18-1
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110-13-4
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83-18-1
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62-53-3
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83-18-1
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