Sodium Hydroxide → (E)-4-(pyrrolidin-1-yl)but-2-en-1-ol

Temperature

60 °C

A solution of 4-(pyrrolidin-1-yl)but-2-yn-1-ol (4.3 g, 31 mmol) in THF (20 ml) was added dropwise to a suspension of lithium aluminum hydride (2.35 g, 62 mmol) in anhydrous THF (8 ml) and the mixture stirred and heated at 60° C. for 2 hours. The mixture was cooled to 5° C. and 2M aqueous sodium hydroxide solution (28 ml) was added dropwise. The resulting suspension was filtered and the volatiles removed from the filtrate by evaporation. The residue was dissolved in a mixture of methylene chloride/ethyl acetate, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on aluminum oxide eluting with methylene chloride/methanol (97/3) to give (E)-4-(pyrrolidin-1-yl)but-2-en-1-ol (3.09 g, 70%).

1. temperatureThe mixture was cooled to 5° C.
2. filtrationThe resulting suspension was filtered
3. customthe volatiles removed from the filtrate by evaporation
4. dissolutionThe residue was dissolved in a mixture of methylene chloride/ethyl acetate
5. dry with materialdried (MgSO4)
6. customthe solvent removed by evaporation
7. customThe residue was purified by column chromatography on aluminum oxide eluting with methylene chloride/methanol (97/3)

ORD record

ord-7c84982c5fdc40919f27811a5f9f7f9d

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897210B2