Acetic Acid → 5-Bromo-2-pyridinepropanol

To a suspension of 3-(5-bromo-2-pyridinyl)-2-propyn-1-ol (0.5 g) and dipotassium azadicarboxylate (3.66 g) in pyridine (40 ml) was added acetic acid (2 ml) and the mixture stirred at room temperature for 24 h, with further additions of acetic acid after 2 h (0.16 ml) and 17 h (2.16 ml). As reduction had only partially gone to completion, further dipotassium azadicarboxylate (3.2 g) and acetic acid (1.86 ml) were added, and stirring continued for 17 h. The mixture was quenched with water (15 ml) and evaporated in vacuo. The residue was co-evaporated with toluene (15 ml) and the residue partitioned between 8% sodium bicarbonate solution (60 ml) and ethyl acetate (60 ml) and the organic phase dried and evaporated in vacuo. The oily residue was purified by FCC using ether and ether-methanol (5%) eluants to afford the title compound as a yellow oil (0.42 g).

1. additionwere added
2. customThe mixture was quenched with water (15 ml)
3. customevaporated in vacuo
4. customthe residue partitioned between 8% sodium bicarbonate solution (60 ml) and ethyl acetate (60 ml)
5. customthe organic phase dried
6. customevaporated in vacuo
7. customThe oily residue was purified by FCC

ORD record

ord-65d6daa4aa4342ff8a2038e551438cdb

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04937251