Triethylamine → (3aR,4R,5R,6aS)-4-((E)-4-(3-Chlorophenoxy)-3-oxobut-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Participants

Reaction Steps

Phosphonate 11 (20.5 g, 70.0 mmol), 2.6 g (62 mmol) of LiCl, and 200 mL of THF were mixed together at 0° C. and 6.10 g (60.4 mmol) of NEt3 was added. Aldehyde 12 (14.0 g, 51.1 mmol) dissolved in 50 mL of CH2Cl2 was then added dropwise. After 1 h, the reaction was poured into 200 mL of a 1/1 mixture of saturated NH4Cl/ethyl acetate, the layers were separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). Combined organic layers were dried over MgSO4, filtered, concentrated, and the residue was chromatographed on silica gel eluting with ethyl acetate/hexanes, 3/2, to afford 16.2 g (72%) of 13 as a white crystalline solid, m.p.=101.0-102.0° C. 1H NMR δ 8.0-7.9 (m, 2 H), 7.62-7.52 (m, 1 H), 7.50-7.38 (m, 2 H), 7.18 (t, J=8.2 Hz, 1 H), 7.0-6.82 (m, 3 H), 6.75-6.70 (m, 1 H), 6.54 (d, J=15.1 Hz, 1 H), 5.32 (q, J=6.2 Hz, 1 H), 5.12-5.05 (m, 1 H), 4.66 (s, 2 H), 3.0-2.8 (m, 3 H), 2.7-2.2 (m, 3 H).

Provenance & Evidence