Tetrahydrofuran → 3-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-hex-5-enoyl)-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-3 (3.0 g, 11.7 mmol) and THF (125 mL) at −78° C. was added NaN(TMS)2 (15.2 mL, 15.2 mmol, 1.0 M in THF) dropwise over 20 minutes. Butenyl-4-triflate (5.0 mL, 29.2 mmol) was added dropwise; after 1 h, the reaction was warmed to 0° C. After 1 h, the reaction was diluted with EtOAc, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 40% EtOAc/hexanes) gave 2-4 as an yellow oil.

Provenance & Evidence