Benzyl Alcohol → HCID 67043395, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dioxolanone 74 (120 mg, 0.444 mmol, 1.00 equiv) in THF (4.5 mL) was cooled to 0° C. and benzyl alcohol (69 μL, 0.67 mmol, 1.5 equiv) was added via syringe followed by a 60% dispersion of NaH in mineral oil (45 mg, 1.1 mmol, 2.5 equiv) which resulted in vigorous evolution of gas. The solution was allowed to stir at 0° C. for 30 min, at which time the reaction was quenched with 4.5 mL NaHCO3, removed from the cold bath and allowed to warm to room temperature. The solution was then poured into H2O (4.5 mL), washed with CH2Cl2 (1×6 mL), acidified to pH<5 with 1N HCl, and then extracted with Et2O (4×6 mL). The combined ethereal phases were dried over MgSO4 and solvent removal by rotary evaporation yielded a white solid which was purified by silica gel column chromatography (70:28:2 hex:EtOAc:HOAc) to yield 75 (114 mg, 88%) as a white solid. Rf=0.39 (60:38:2 EtOAc:Hex:HOAc); 1H NMR (500 MHz, CDCl3) δ 7.35 (m, 5H, ArH), 5.20 (s, 2H, PhCH2), 5.07 (m, 1H, vinyl H), 3.00 (d, 1H, J=16.7 Hz, C(O)CH2), 2.76 (d, 1H, J=16.7 Hz, C(O)CH2), 2.41 (m, 2H, CHCH2), 1.67 (d, 3H, J=0.7 Hz, CH3), 1.54 (d, 3H, J=0.7 Hz, CH3); 13C NMR (100 MHz, CDCl3) δ 176.43, 174.60, 136.79, 135.21, 128.71, 128.64, 128.61, 116.45, 75.41, 67.95, 42.69, 38.14, 26.06, 18.09; IR (neat film) 3483 (br m), 2968 (m), 1736 (s), 1498 (w), 1195 (s) cm−1; HRMS (ESI) m/z calcd for C16H20O5Na (M++Na+) 315.1208; observed 315.1214; [α]D=−18° (c 2.98, CHCl3).

Provenance & Evidence