Sodium Hydroxide → 3,5-Dimethyl-1H-pyrrole-2-carbaldehyde

To a mixture of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1.67 g, 10 mmol) in dimethylforamide (10 mL) was added benzotriazol-1-yloxytris (dimethylamino)- phosphonium hexafluorophosphate (BOP reagent, 6 g, 13.5 mmol) followed by 3 mL diisopropylethylamine. After stirring for 5 minutes, 1 mL of N,N-dimethylethylendiamine was added and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added 25 mL of 1N sodium hydroxide and 25 mL of brine. After stirring for 30 minutes, the reaction mixture was poured into water (100 mL) and extracted (3×200 mL) with 10% of methanol in dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and evaporated using a rotary evaporator. The residue which remained was purified by chromatography (silica gel column, 5%-10% methanol in dichioromethane) to give 1 g (42%) of 5-formyl-2,4-dimethyl-1H-pyrrole-3-(carboxylic acid (2-dimethylamino-ethyl)-amide.

1. stirringthe mixture was stirred at room temperature for 24 hours
2. stirringAfter stirring for 30 minutes
3. extractionextracted (3×200 mL) with 10% of methanol in dichloromethane
4. dry with materialdried over anhydrous sodium sulfate
5. customevaporated
6. customa rotary evaporator
7. customThe residue which remained was purified by chromatography (silica gel column, 5%-10% methanol in dichioromethane)

ORD record

ord-fb97b7389c8241efbea33d30ddd4851e

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119090B2