CID 406 → HCID 67998516, compound

Participants

Reaction Steps

To a slurry of NaH (60% dispersion in mineral oil, 0.608 g, 15.2 mmol) in THF (50 mL) was added ethyl 2-(diethoxyphosphoryl)acetate (3.25 mL, 16.2 mmol). After about 30 min, the phosphonate solution was added to a flask charged with (3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentanone (2.6 g, 10.14 mmol). After about 20 h, EtOAc (20 mL) and saturated aqueous NH4Cl (20 mL) were added. The organic layer was removed concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (20-60%) to provide ethyl 2-((3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentylidene)acetate (3.3 g, 100%) as an oil. LC/MS (Table 1, Method a) Rt=3.91, 3.96 min; MS m/z: 327 (M+H)+.

Provenance & Evidence