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

To a solution of (E)-2-(4-hydroxybut-2-enyloxy)-6-nitrobenzonitrile (Example 199d) (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-e775d95a9eee47c8ae0e2b68448dae06

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181276B2