Water → HCID 54391081, compound

Participants

Reaction Steps

Tributyltin hydride (450 μL, 1.7 mmol) was added dropwise over 1-1/2 hours to a stirred solution of the ene-one ester from Step A (320 mg, 1 mmol) and tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) in dry THF (5 mL) at ambient temperature under N2. After standing at 20° C. overnight the light-brown solution was distributed between water (100 mL) and ether (150 mL). The organic layer was separated and washed with water (2×100 mL), dried and evaporated. The residual oil (1 major spot on TLC with Rf 0.39 vis-a-vis 0.35 for the starting ene-one ester on Whatman MK6F silica using CHCl3 -MeOH; 99:1 as eluent) was chromatographed on a Still column to obtain the product (260 mg, 81%) as a pale amber gum; NMR (CDCl3) δ: 2.5-2.525 (2H, m, --C2CO2 --), 2.57-2.73 (2H, m, -- COC2C(OH)--), 2.77 (2H, t, J=7.5 Hz, AR-CH2CH2CO-), 2.98 (2H, t, J=7.5 Hz, Ar-CH2CH2CO-), 3.71 (3H, s, --CO2C3), 4.45-4.51 (H, m, --CH(OH)--).

Provenance & Evidence