Sodium Methoxide → methyl 4-iodo-1H-pyrrole-2-carboxylate

2,2,2-Trichloro-1-(4-iodo-1H-pyrrol-2-yl)-ethanone 57c (47 g, 136 mmol) was dissolved in 265 mL of methanol followed by dropwise addition of a solution of sodium methoxide (17.23 g, 163 mmol) in 200 mL of methanol. The reaction mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure. The residue was diluted with 20 mL of water and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure to obtain the title compound 4-iodo-1H-pyrrole-2-carboxylic acid methyl ester 57d (32.2 g, yield 92.5%) as a grey solid.

1. concentrationThe mixture was concentrated under reduced pressure
2. additionThe residue was diluted with 20 mL of water
3. extractionextracted with ethyl acetate (30 mL×3)
4. washThe combined organic extracts were washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customto remove the drying agent
8. concentrationconcentrated under reduced pressure

ORD record

ord-7e4ccba829bf4dabaead2a78dbccec1e

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2