Tetrahydrofuran → (1R*,2R*)-Acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester

Participants

Reaction Steps

To a flame dried round bottom flask, [Rh(COD)Cl]2 (4.3 mg, 0.008 mmol DPPF (9.6 mg, 0.017 mmol), 1 (50 mg, 1.39 mmol), and sodium acetate (142 mg, 1.74 mmol) were added followed by addition of THF (2 mL) and triethylamine hydrochloride (239 mg, 1.74 mmol). The mixture was heated at reflux for 3 hours and the solvents were removed in vacuo. The resulting mixture was purified by flash chromatography (30% ethyl acetate in hexanes) to give 2 as a crystalline solid (41 mg), 63%). Rf=0.26 on silica gel (20% ethyl acetate:hexanes); mp 67-68° (Et2O); IR (KBr, cm−1) 1H NMR (400 MHz, CDCl3) δ 7.54-7.53 (1H, m), 7.29-7.24 (2H, m), 7.10-7.08 (1H, m), 6.50 (1H, dd, J=3.9, 1.3 Hz), 5.85 (1H, dd, J=9.9, 3.1 Hz), 5.59 (1H, ddd, J=9.0, 2.8, 1.9 Hz), 4.92 (1H, d, J=9.0 Hz), 2.64 (1H, s), 2.12 (3H, s); 13C NMR (400 MHz, CDCl3) δ 171.3, 135.2, 131.5, 129.5, 128.3, 126.7, 126.0, 125.4, 75.3, 71.7, 21.2. HRMS calcd for C12H12O3 (M): 204.0786. Found: 204.0791.

Provenance & Evidence