2,6-Lutidine → HCID 86705576, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 392 (15.5 g, 60.1 mmol), 2,6-lutidine (21.0 ml, 180 mmol) and DCM (125 mL) cooled to 0° C. and maintained under N2 was added dropwise triethylsilyl trifluoromethanesulfonate (17.5 g, 66.1 mmol). The reaction was stirred at 0° C. for 1 h then warmed to RT and stirred for 18 h. The reaction was quenched by adding satd. aq. NH4Cl and extracted with DCM. The organic extract was washed organic with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by SiO2 chromatography (SNAP 100) eluting with EtOAc/hexane (9:1) to afford 18.9 g (76%) of (S)-ethyl 4-iodo-2-(triethylsilyloxy)butanoate (396) as a yellow oil.

Provenance & Evidence