Ethylene Oxide → HCID 17912558, compound

To a solution of 3,5-dichloropyridine (4.0 g, 27.0 mmol) in THF (70 mL) was added LDA (1.8 M in THF/heptane/ethylbenzene, 22.0 mL, 39.6 mmol) at −78° C. and the mixture was stirred at the same temperature for 2 h, and then ethylene oxide (1.2 M in THF, 25 ml, 30.0 mmol) was added. The reaction mixture was allowed to warm to room temperature gradually and stirred for 1 h at room temperature. The reaction mixture was quenched by adding saturated aqueous NH4Cl solution and extracted with EtOAc. The organic layer was washed with brine (2 times) and dried over MgSO4. After the solvent was removed, the residue was purified by column chromatography on silica gel to give compound B1-1 (3.1 g, 60%) as a yellow solid.

1. stirringstirred for 1 h at room temperature
2. customThe reaction mixture was quenched
3. additionby adding saturated aqueous NH4Cl solution
4. extractionextracted with EtOAc
5. washThe organic layer was washed with brine (2 times)
6. dry with materialdried over MgSO4
7. customAfter the solvent was removed
8. customthe residue was purified by column chromatography on silica gel
9. customto give compound B1-1 (3.1 g, 60%) as a yellow solid

ORD record

ord-8808a2b160e0452e9a0a9f9e31371e35

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2