2,6-Di-tert-butyl-4-methylpyridine → HCID 66745608, compound

To a solution of (E)-2-(4-hydroxybut-2-enyloxy)-6-nitrobenzonitrile (Example 184d) (0.50 g, 2.13 mmol) and 2,6-di-tert-butyl-4-methylpyridine (2.18 g, 10.65 mmol) in CH2Cl2 (15.0 mL) at rt, was added trimethyloxonium tetrafluoroborate (1.58 g, 10.65 mmol) under a nitrogen atmosphere. After 1 h at rt, the reaction was quenched with water (50 mL) and extracted with EtOAc (4×50 mL). The combined extract was washed with water, 1.5M HCl, saturated aqueous NaHCO3 and brine, and was dried over anhydrous MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using the solvent gradient hexanes→hexanes/EtOAc (3:7), to give 0.25 g (72%) of the title compound as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 7.84-7.92 (m, 2H), 7.68-7.73 (m, 1H), 5.82-6.03 (m, 2H), 4.82-4.88 (m, 2H), 3.87-3.93 (m, 2H), 3.21 (s, 3H).

1. customthe reaction was quenched with water (50 mL)
2. extractionextracted with EtOAc (4×50 mL)
3. extractionThe combined extract
4. washwas washed with water, 1.5M HCl, saturated aqueous NaHCO3 and brine
5. dry with materialwas dried over anhydrous MgSO4
6. customThe filtrate was evaporated
7. customthe residue was purified by chromatography on silica gel using the solvent gradient hexanes→hexanes/EtOAc (3:7)

ORD record

ord-ff2da4496c824b02b38b5c65ec365d80

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000054B2