Water → HCID 58042403, compound

Sodium hydride dispersion (60%, 1.22 g, 30.5 mmol) was suspended in anhydrous THF (40 mL) under a nitrogen atmosphere. A solution of cyclobutanol (2.0 g, 27.7 mmol) in THF (10 mL) was added dropwise at room temperature then the reaction was stirred 1 hour at room temperature. 2,3-dichloropyridine (5.0 g, 33.8 mmol) was added and the reaction mixture was stirred at 60° C. under nitrogen for 16 hours. Water (50 mL) was added and the reaction mixture was concentrated in vacuo. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with 3% EtOAc in heptane to afford the title compound as a clear oil (3.7 g, 72%):

1. stirringthe reaction mixture was stirred at 60° C. under nitrogen for 16 hours
2. concentrationthe reaction mixture was concentrated in vacuo
3. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
4. dry with materialThe combined organics were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude material was purified by silica gel chromatography
8. washeluting with 3% EtOAc in heptane

ORD record

ord-431d7d59cb3540c89f61fa8f75473a6a

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2