Tributyltin Chloride → HCID 58207969, compound

Participants

Reaction Conditions

Reaction Steps

LDA (0.55M 1.1 mmol, 2M) was added to a RBF containing THF (5 mL) cooled to −78° C. A solution of tert-butyl isopropyl(thiazol-2-yl)carbamate (242 mg, 1 mmol) in THF (5 mL) was added via cannula and the resulting solution stirred for 2 h at −78° C. Tributyltin chloride (0.27 mL, 1 mmol) was added and the reaction mixture allowed to slowly warm to room temperature then stirred overnight. The reaction mixture was then quenched with NH4Cl (2 mL, sat. aq.) and diluted with water. The mixture was then extracted with EtOAc (3×25 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The product was isolated via column chromatography (SiO2, 2% EtOAc/heptane) to afford the product (214 mg, 40% yield) as a colorless oil.

Provenance & Evidence