Benzoic Acid → HCID 22218642, compound

Participants

Reaction Steps

Triphenylphosphine (1.44 g, 5.49 mmol) and benzoic acid (0.60 g, 4.91 mmol) were added to a solution of cis-3-(2-naphthyl)-indan-1-ol, 6a and 6b (0.645 g, 2.48 mmol) in anhydrous THF (20 mL). The reaction was treated dropwise with a solution of DEAD in THF (4.95 M, 1 mL) then stirred under nitrogen atmosphere at room temperature. After 3 h, the reaction solution was directly filtered through a pad of silica and condensed. The resulting residue was purified by radial chromatography (4 mm plate, 10% ethyl acetate/hexanes) yielding a mixture of enantiomers 8a and 8b as an off-white solid (0.72 g, 80%): Rf=0.46 in 10% ethyl acetate/hexanes; 1H-NMR (CDCl3) δ 8.08–8.05 (m, 2H), 7.84–7.78 (m, 3H), 7.71 (bs, 1H), 7.58–7.41 (m, 4H), 7.35–7.29 (m, 2H), 7.24 (dd, 2H, J=5.7, 2.7), 7.07–7.04 (m, 1H), 6.62 (dd, 1H, J=6.3, 1.9), 4.88 (t, 1H, J=7.7), 2.83 (ddd, 1H, J=2.2, 7.7, 14.6), 2.69–2.60 (ddd, 1H, J=6.6, 7.98, 14.6).

Provenance & Evidence