Acetic Acid → HCID 66869262, compound

Temperature

50 °C

Add dropwise a solution of N-tert-butyl-N′-(4-fluorobenzylidene)hydrazine (Tetrahedron, 1986, 42, 4223-4234) (8.4 g, 43.2 mmol) in acetonitrile (43 mL) to a well stirred mixture of ethyl propiolate (4.4 mL, 43.2 mmol) and acetic acid (37 mL, 648 mmol) at RT. Warm the mixture at 50° C. for 2 days and at 60° C. for 1 day. Cool at RT and dilute with dichloromethane (250 mL). Wash the mixture with water (50 mL), a saturated aqueous solution of Na2CO3 (2×50 mL), dry (MgSO4), concentrate and purify (Biotage system eluting with CH2Cl2). Dissolve the yellow solid obtained in dichloromethane (43 mL) and acetic acid (37 mL) and bubble a stream of O2 at RT for 10 days. Dilute the mixture with dichloromethane (100 mL) and wash with a saturated aqueous solution of Na2CO3 (2×50 mL), dry (MgSO4) and concentrate and purify (Biotage system eluting with CH2Cl2) to provide the desired compound as yellow solid (6.4 g, 51% yield).

1. temperatureCool at RT
2. washWash the mixture with water (50 mL)
3. dry with materiala saturated aqueous solution of Na2CO3 (2×50 mL), dry (MgSO4)
4. concentrationconcentrate
5. custompurify
6. wash(Biotage system eluting with CH2Cl2)
7. dissolutionDissolve the yellow solid
8. customobtained in dichloromethane (43 mL)
9. customacetic acid (37 mL) and bubble a stream of O2 at RT for 10 days
10. additionDilute the mixture with dichloromethane (100 mL)
11. washwash with a saturated aqueous solution of Na2CO3 (2×50 mL)
12. dry with materialdry (MgSO4)
13. concentrationconcentrate
14. custompurify
15. wash(Biotage system eluting with CH2Cl2)

ORD record

ord-e93a3ee4317849508fc9ea86a04af738

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863310B2