(E)-8-methylnon-6-enoyl chloride

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (−78° C.) solution of (R)-4-benzyloxazolidin-2-one (2.817 g, 15.899 mmol) in 40 mL of THF, was added n-BuLi (6.4 mL, 15.899 mmol, 2.5 M in hexane). The resulting mixture was stirred at −78° C. under N2 for 15 min. and then (E)-8-methylnon-6-enoyl chloride (3.000 g, 15.899 mmol) was added. After stirring at −78° C. for 1 h and then being warmed to room temperature under N2 for overnight, the reaction mixture was quenched with 80 mL of NH4Cl solution and extracted with dichloromethane (60 mL×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (4.468 g, 85% yield). GC-MS: tR=6.2 min; m/z 329 (M+). After stirring at −78° C. for 1 h being warmed to room temperature under N2 for overnight the reaction mixture was quenched with 80 mL of NH4Cl solution extracted with dichloromethane (60 mL×3) The combined organic extracts were dried (Na2SO4) filtered concentrated under reduced pressure The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes