HCID 86676433, compound → HCID 67211343, compound

Participants

Reaction Steps

A solution of [4-((3aR,6S,7aR)-6-tert-Butyl-2-thioxo-tetrahydro-benzo[1,3]dioxol-3a-yl)-phenyl]-acetic acid ethyl ester (297 mg, 0.80 mmol) in triethylphosphite (3 mL) was slowly added to a solution of triethylphosphite (10 mL) heated to reflux—rate of addition was such that the reaction temperature exceeded 150. After refluxing overnight, the solvent was removed under vacuum and the crude reaction mixture was loaded on top of a silica column and eluted with an ethyl acetate/hexanes gradient to afford 145 mg of the title compound. 1H NMR (500 MHz, CDCl3): 7.32 (d, J=8 Hz, 2 H), 7.20 (d, J=8 Hz, 2 H), 6.10 (m, 1 H), 4.12 (q, J=7 Hz, 2 H), 3.57 (s, 2 H), 2.52-2.32 (m, 2 H), 2.26-2.18 (m, 1 H), 2-1.9 (m, 2 H), 1.38-1.2 (m, 5 H), 0.91 (s, 9 H).

Provenance & Evidence