Lithium diisopropylamide → 1-(Pyridazin-3-yl)ethan-1-ol

Temperature

-60 °C

To a solution of LDA (23.4 mL, 42.1 mmol, 1.8 M in THF) in THF (150 mL) was added slowly a solution of compound 1 (3.6 g, 21.05 mmol) in THF (77 mL) at −60° C. under a N2 atmosphere. After being stirred at −60° C. for 1 h, a solution of compound 2 (7.05 g, 18.9 mmol)) in THF (23 mL) was added slowly to the above solution. The resulting mixture was stirred at −60° C. for 2 h. The reaction mixture was quenched with water (15 mL). The aqueous layer was extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel (petroleum:ethyl acetate, 10:1) to give compound 3 (2.5 g, yield 26%) as a yellow solid.

1. stirringThe resulting mixture was stirred at −60° C. for 2 h
2. customThe reaction mixture was quenched with water (15 mL)
3. extractionThe aqueous layer was extracted with EtOAc (3×40 mL)
4. washThe combined organic layers were washed with brine (20 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure to dryness
7. customThe residue was purified by column chromatography on silica gel (petroleum:ethyl acetate, 10:1)

ORD record

ord-7734bd19058340a4acf9a5ea71277674

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212153B2