Water → HCID 83214412, compound

To a suspension of 1.24 g of sodium hydride (60% oil dispersion; 31 mmol) in 90 mL of THF were added dropwise 3.27 g of 3-pyridinemethanol (30 mmol) in 10 mL of dry THF at room temperature over 5 min. The resulting white suspension was stirred at room temperature for an hour, to which was then added dropwise 6.27 g of tert-butyl 2-bromopropionate (30 mmol) in 10 mL of dry THF at room temperature over 5 min. The mixture was stirred at room temperature for 11.5 hours. After adding water, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and evaporated. The residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=1:1) to give 4.01 g of tent-butyl (pyridin-3-yl)methoxyacetate (Yield: 56.3%) as a dark brown oil.

1. stirringThe mixture was stirred at room temperature for 11.5 hours
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. customdried
5. customevaporated
6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=1:1)

ORD record

ord-69956113627647b696786b9af1602342

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026239B2