Phenylacetylene → HCID 22097746, compound

Temperature

-78 °C

To a 500 mL, three necked round bottomed flash with a stirring bar, low temperature thermometer, argon inlet and a septum was added dry THF (100 mL) and ethynylbenzene (60 mmol, 6.1 mL). This solution was cooled to -78° C. and n-butyllithium (60 mmol, 24 mL of a 2.5M solution in hexane) was added with a syringe at such a rate that the temperature was maintained below -50° C. When the addition was complete, the solution was aged 30 min then a solution of 3(R,S)-benzoylazetidinone (15 mmol, 2.87 g) in THF (50 mL) was added slowly with a syringe, maintaining the temperature below -60° C. The resulting solution was aged 1 h at -78° C. then warmed to 0°C. The reaction was quenched at 0°C. by addition of saturated, aqueous NH4Cl solution. The mixture was diluted with EtOAc and the layers were separated. The organic phase was washed with H2O and brine. Drying (MgSO4), filtration and removal of the solvents in vacuo gave 3(R,S)-phenylethynylazetidinone (15-2) as a crystalline solid, which was used in Step B without further purification. ##STR139##

1. temperaturewas maintained below -50° C
2. additionWhen the addition
3. temperaturemaintaining the temperature below -60° C
4. waitThe resulting solution was aged 1 h at -78° C.
5. temperaturethen warmed to 0°C
6. customThe reaction was quenched at 0°C. by addition of saturated, aqueous NH4Cl solution
7. additionThe mixture was diluted with EtOAc
8. customthe layers were separated
9. washThe organic phase was washed with H2O and brine
10. customDrying
11. filtration(MgSO4), filtration and removal of the solvents in vacuo

ORD record

ord-a11d602de70a4d14ad2e1cb85f3dd25b

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05852045