Imidazole → HCID 53720908, compound

A solution of imidazole (2.32 g, 34.1 mmol), the title compound of Step 10 (5.0 g, 22.7 mmol) and NaHCO3 (6.58 g, 78.3 mmol) in anhydrous EtOH (40 mL) was refluxed overnight in a modification of the procedure of Bach et al, [J. Am. Chem. Soc., 79, 2221-2225 (1957)]. After filtration, the filtrate was concentrated to a yellow oil. The oil was dissolved into a 1.0M KOH solution (10 mL) and was extracted with EtOAc (3×5 mL). The organic layer was washed with a 5% NaHCO3, solution (5 mL), H2O (5 mL), and brine (5 mL) and then was dried over MgSO4. The filtrate was concentrated and purified by medium pressure column chromatography on silica gel [eluting with NH4OH-EtOH-CHCI3 (1:4: 94)] to give the title compound as an oil (1.69 g, 30% yield). The proton spectral data were consistent with the proposed structure.

1. filtrationAfter filtration
2. concentrationthe filtrate was concentrated to a yellow oil
3. dissolutionThe oil was dissolved into a 1.0M KOH solution (10 mL)
4. extractionwas extracted with EtOAc (3×5 mL)
5. washThe organic layer was washed with a 5% NaHCO3, solution (5 mL), H2O (5 mL), and brine (5 mL)
6. dry with materialwas dried over MgSO4
7. concentrationThe filtrate was concentrated
8. custompurified by medium pressure column chromatography on silica gel [eluting with NH4OH-EtOH-CHCI3 (1:4: 94)]

ORD record

ord-3b60c516a4544c46829da71be41b36cc

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05373017