Diethyl Carbonate → HCID 69967939, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(N-Boc-N-ethylamino)-6-pyridylacetate LDA (0.018 mol) was prepared in THF (30 mL), cooled to -78° C., and 2-(N-Boc-N-ethylamino)-6-picoline (3.5 g, 15 mmol) was added, forming a deep red solution. After 15 min, diethyl carbonate (2.2 mL, 17.9 mmol) was added, the burgundy-colored solution was stirred at -78° C. for an additional 15 min, then the reaction was quenched with saturated NH4Cl. The mixture was warmed to RT and extracted with EtOAc(3×30 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. Silica gel chromatography (10% EtOAc/hexane) gave the title compound as colorless oil: MS (ES) m/e 309 (M+H)+.

Provenance & Evidence