Cesium carbonate → HCID 68108607, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of step B (230 mg, 0.66 mmol), sodium benzenesulfinate (132 mg, 0.80 mmol), di-palladium-tris(dibenzylideneacetone) (60 mg, 0.07 mmol), cesium carbonate (322 mg, 0.99 mmol) and xantphos (76 mg, 0.13 mmol) was suspended in anhydrous toluene (4 mL). The reaction flask was purged with argon and heated at 110° C. for 5 h. After cooling, the reaction mixture was diluted with dichloromethane and filtered through a celite bed. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give a single enantiomer of 6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-yl acetate (150 mg, 56%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.01-7.92 (m, 3H), 7.83 (d, J=1.8 Hz, 1H), 7.61-7.48 (m, 3H), 5.36-5.28 (m, 1H), 3.06-2.73 (m, 4H), 2.28-2.09 (m, 2H), 2.05 (s, 3H).

Provenance & Evidence