Diethyl Ether → HCID 178473086, compound

Temperature

60 °C

In a dry flask, under argon atmosphere, sodium (317 mg, 13.8 mmol, Eq: 1.00) was added portionwise to ethanol (9.0 ml). (The temperature increased to 60° C.). The reaction mixture was cooled at 0° C. Then Diethyl oxalate (2.01 g, 1.87 ml, 13.8 mmol, Eq: 1.00) was added dropwise followed by 4-acetylbenzonitrile (2 g, 13.8 mmol, Eq: 1.00) in Ethanol (3.00 ml). A white solid appeared. The reaction was stirred with mechanical stirrer overnight and monitored by TLC. Then the reaction mixture was concentrated in vacuo. The residue was cooled at 0° C. and water was added to the flask. 1M HCl was added to this solution (pH=3), then the solution was extracted two times with EtOAc. The organic layer was washed three times with 20 mL Brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to give an off-white solid. This off-white solid was mixed with Ether at 0° C. The suspension was filtered to give a white solid (2.082 g, 61.6%).

1. temperatureThe reaction mixture was cooled at 0° C
2. concentrationThen the reaction mixture was concentrated in vacuo
3. temperatureThe residue was cooled at 0° C.
4. additionwater was added to the flask
5. addition1M HCl was added to this solution (pH=3)
6. extractionthe solution was extracted two times with EtOAc
7. washThe organic layer was washed three times with 20 mL Brine
8. dry with materialThe resulting organic layer was dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give an off-white solid
12. filtrationThe suspension was filtered

ORD record

ord-c85db2a82c604e32bfc77c3563a750b6

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073911B2