Triethyl 2-fluoro-2-phosphonoacetate → (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester

Participants

Reaction Steps

Following General Procedure B and using triethyl 2-fluoro-2-phosphonoacetate (5.6 mL, 27.6 mmol), THF (50 mL), n-BuLi (17.3 mL, 1.6 M in hexane, 27.6 mmol), and 1-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one (Intermediate 14, 2.8 g, 9.2 mmol) in THF (10 mL), followed by flash column chromatography on silica gel (3% EtOAc-hexane), the title compound was obtained as a mixture containing minimal 2-Z isomer (3.3 g). The mixture was used directly in the next reaction.

Provenance & Evidence