Acetic Acid → HCID 58560719, compound

Participants

Reaction Steps

To a solution of (2R,3R)-1-(4-(dimethoxymethyl)phenyl)decane-2,3-diol (M) (0.38 g, 1.17 mmol) in THF (12 mL) at room temperature was added aqueous acetic acid (6.2 mL, 2.5 M). The reaction mixture was stirred for two hours until TLC indicated completion of the reaction at which time saturated aqueous NaHCO3 was added, and the mixture extracted with ether. The collected organic layers were washed with brine, dried with MgSO4, filtered, and concentrated to yield the free aldehyde (0.309 g, 1.11 mmol, 95%). The crude free aldehyde was dissolved in acetone (5 mL) and to this mixture was added p-toluenesulfonic acid (33 mg, 0.17 mmol). The reaction mixture was stirred overnight, at which time TLC indicated completion of the reaction. Upon completion, triethylamine (24 μL, 0.17 mmol) was added and solvent was evaporated. Flash chromatography of the residue gave the title compound (0.26 g, 0.82 mmol, 74%). 1H NMR (CDCl3, 300 MHz) δ 9.90 (1H, s), 7.82 (2H, d, J=8.1 Hz), 7.42 (2H, d, J=7.8 Hz), 3.88-3.83 (1H, m), 3.70-3.65 (1H, m), 2.94 (2H, d, J=5.7 Hz), 1.51-1.29 (12H, m), 1.37 (3H, s), 1.35 (3H, s), 0.88 (3H, t, J=4.8 Hz); LRMS (APCI+) calcd for C20H30O3 [M+H]: 319.2; found 319.5

Provenance & Evidence