4-Chloropyridine → HCID 86695935, compound

Temperature

-78 °C

4-Chloropyridine (5 g, 44.0 mmol) hydrochloride salt was dried by azeotropic distillation with anhydrous toluene in a round bottomed flask. To this, anhydrous THF (100 mL) was added under nitrogen atmosphere and cooled to −78° C. After 15 min, LDA, 2M in THF/heptane/ethylbenzene (48.4 mL, 97 mmol) was added dropwise and the reaction stirred for 30 min. Oxetan-3-one (3.81 g, 52.8 mmol) was then added and reaction was stirred for 5 min at −78° C. and then cold bath was removed and reaction was allowed to warm to room temperature gradually (˜1 h). The reaction was quenched by addition of aqueous ammonium chloride and organics extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried and concentrated under reduced pressure to afford 3-(4-chloropyridin-3-yl)oxetan-3-ol (3.8 g, 20.47 mmol, 46% yield) as a yellow oil.

1. customreaction
2. stirringwas stirred for 5 min at −78° C.
3. customcold bath was removed
4. customreaction
5. temperatureto warm to room temperature gradually (˜1 h)
6. customThe reaction was quenched by addition of aqueous ammonium chloride
7. extractionorganics extracted with ethyl acetate (3×50 mL)
8. customThe combined organic extracts were dried
9. concentrationconcentrated under reduced pressure

ORD record

ord-259764ecc5364b66aa0490ad1887a306

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969564B2