反应详情

Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate (3.8 g, 14.0 mmol) [prepared as in Example 7, Step (a)] was dissolved in a 1:1 mixture of MeOH-THF (100 ml) and cooled in an ice bath under argon. A solution of 0.4 M lithium hydroxide (69 ml) was added and the reaction mixture was stirred at room temperature. After 2 h, the reaction mixture was poured into 1 M HCl/ice and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The solid residue was redissolved in DMF (40 ml) and heated at reflux. After 20 min the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to dryness. Purification on a Florisil® column (hexane-ethyl acetate, 9:1) gave 4-(1-methylpyrrol-2-yl-methyl)nitrobenzene (2.53 g, 82%) as a solid. ##STR39##

1. temperaturecooled in an ice bath under argon
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with water
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe solid residue was redissolved in DMF (40 ml)
7. temperatureheated
8. temperatureat reflux
9. additionAfter 20 min the reaction mixture was poured into ice/water
10. extractionextracted with ethyl acetate
11. washThe organic layer was washed with water
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated to dryness
14. customPurification on a Florisil® column (hexane-ethyl acetate, 9:1)