Tetrahydrofuran → HCID 21251054, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of alcohol from Step 2 above (121 mg, 0.27 mmol) in 3 mL of toluene was added 0.113 mL (0.65 mmol) of i-Pr2NEt followed by 0.024 mL (0.32 mmol) of SOCl2. The solution was stirred 1 h at 0° C. followed by the addition of the enolate generated as follow: to a solution of ethyl 4-pyridyl acetate (178 mg, 1.08 mmol) and HMPA (0.188 mL, 11.08 mmol) in 4 mL of THF, was slowly added 2.2 mL (1.08 mmol) of a 0.5 M solution of KHMDS in toluene and the resulting solution was stirred 10 minutes at room temperature. The resulting cloudy solution was stirred 25 minutes, quenched with a saturated aqueous NH4Cl solution and diluted with ethyl acetate/saturated NaHCO3 solution. The aqueous layer was extracted with ethyl acetate and the combined organic layer were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was used directly for the next step without any purification.

Provenance & Evidence