Sodium Chloride → Methyl 5-methyl-1H-pyrrole-3-carboxylate

A solution of methyl acrylate (0.523 mL, 5.81 mmol) and 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.215 g, 5.81 mmol) in diethyl ether (16.5 mL) and DMSO (8.5 mL) were added dropwise to a stirred suspension of sodium hydride (60% dispersion) (0.372 g, 9.29 mmol) in diethyl ether (25 mL) under nitrogen. The resulting suspension was stirred at room temperature for 2 hours. The reaction mixture was poured into 2% sodium chloride solution (200 mL), layers separated and the aqueous extracted with Et2O (4×50 mL), the organic layers were combined washed with water (50 mL), dried over Na2SO4, filtered and evaporated to afford beige solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford the desired compound as a white solid (0.527 g, 65.2% yield); 1H NMR (400.132 MHz, CDCl3) δ 2.19 (3H, s), 3.72 (3H, s), 6.23 (1H, m), 7.21 (1H, m), 8.09 (1H, s); m/z (LC-MS, ESI+), RT=1.30 min (no mass ion detected).

1. customseparated
2. extractionthe aqueous extracted with Et2O (4×50 mL)
3. washthe organic layers were combined washed with water (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customto afford beige solid
8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% ethyl acetate in isohexane
9. customPure fractions were evaporated to dryness

ORD record

ord-675a74c2c3f04b508ffc62ad44509ecc

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2