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-010c1dd6c0984db4829eef3a58a5bab2

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633186B2