Diethyl cyanophosphonate → HCID 57419479, compound

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (1 g, 4.74 mmol) in anhydrous THF (15 ml) at −10° C. was added 2M lithium diisopropylamide in THF (0.242 ml, 0.483 mmol) dropwise. The resulting mixture was stirred at −10° C. for 15 min before diethylcyanophosphonate (0.791 ml, 5.21 mmol) was added dropwise. Following the addition, the mixture was allowed to warm to room temperature, and was stirred at room temperature for 3 h. The mixture was cooled to −78° C. and borontrifluoride diethyl etherate (1.196 ml, 9.52 mmol) was added dropwise. Following the addition, the mixture was stirred at −78° C. for 1 h and was then allowed to warm to room temperature and was stirred at room temperature for 16 h. The mixture was concentrated in vacuo, and the residue was partitioned between EtOAc (50 mL) and H2O (2×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo, and the crude product was purified by column chromatography on silica gel using 9:1 EtOAc:hexanes as the eluent. The title compound was obtained as an tan solid (0.72 g, 69%).

1. additionwas added dropwise
2. additionthe addition
3. temperatureThe mixture was cooled to −78° C.
4. additionthe addition
5. stirringthe mixture was stirred at −78° C. for 1 h
6. temperatureto warm to room temperature
7. stirringwas stirred at room temperature for 16 h
8. concentrationThe mixture was concentrated in vacuo
9. customthe residue was partitioned between EtOAc (50 mL) and H2O (2×50 mL)
10. dry with materialThe organic layer was dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customthe crude product was purified by column chromatography on silica gel using 9:1 EtOAc

ORD record

ord-999b90a09c44417cb3ddcd2de325b990

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685991B2