Ethyl Acetate → HCID 86653781, compound

Participants

Reaction Steps

A stirred solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butan-1-ol (640 mg, 1.58 mmol) in 10 mL CH2Cl2 at 0° C. was treated with a suspension of Dess-martin periodonate (860 mg, 2.03 mmol) in CH2Cl2 (4 mL) and the pale yellow cloudy solution stirred at room temperature for 1.25 h. The cloudy white solution was poured over a solution of 10 mL 1.0 M NaHCO3 containing ˜0.5 g Na2S2O3 and 20 mL EtOAc added, the layers separated and the aqueous phase extracted 3×20 mL EtOAc. The combined organics were washed with 20 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to a yellow-white solid. The solid was dissolved into 5 mL EtOAc, filtered and the residual solids rinsed with EtOAc. The combined washings were stored overnight at 2° C., concentrated and purified by flash chromatography (gradient elution, 0-20% EtOAc/heptanes) collecting 530 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanal. MS M++H at 403 m/z; 1H NMR (400 MHz, CDCl3) δ=9.67 (t, 1H), 7.52-7.48 (m, 2H), 7.45-7.36 (m, 6H), 4.75 (s, 2H), 4.74 (s, 2H), 2.69 (t, 2H), 2.44 (td, 2H), 2.27 (s, 3H), 2.24 (s, 6H), 1.84 (pent, 2H) ppm.

Provenance & Evidence