Ethanolamine → 1-(2-Hydroxyethyl)-2,5-dimethylpyrrole

Temperature

115 °C

A mixture of hexan-2,5-dione (5 g), ethanol amine (26.7 g) and pivalic acid (23.26 g) in a solvent mixture containing n-heptane: tetrahydrofliran: toluene (4:1:1, 50 mL) was refluxed with stirring at 110-120° C. Water formed during the reaction was removed azeotropically during 3 to 4 hrs. The reaction mixture was cooled and the solvent was removed. The residue obtained was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (30 mL), water (30 mL), and then with brine (30 mL), dried (Na2SO4) and the solvent was evaporated. The crude compound obtained as an oily mass, was purified by column chromatography (silica gel 100-200), using ethyl acetate:hexane (2:8) as an eluent to obtain the title compound.

1. customwas removed azeotropically during 3 to 4 hrs
2. temperatureThe reaction mixture was cooled
3. customthe solvent was removed
4. customThe residue obtained
5. washwashed with saturated sodium bicarbonate solution (30 mL), water (30 mL)
6. dry with materialwith brine (30 mL), dried (Na2SO4)
7. customthe solvent was evaporated
8. customThe crude compound obtained as an oily mass
9. customwas purified by column chromatography (silica gel 100-200)

ORD record

ord-e2a83902dbf645bebd5aa023a6ccea25

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323491B2