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 vacuio. 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