Propanedioic acid, 2,2-bis(hydroxymethyl)-, 1,3-diethyl ester → Diethyl 2-[(4,4',4''-trimethoxytrityl)oxymethyl]-2-hydroxymethylmalonate

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Reaction Steps

Referring to scheme 1, diethyl bis-(hydroxymethyl)malonate (11.5 g, 55 mmol) was treated overnight with 4,4′,4″-trimethoxytrityl chloride (19.2 g, 52 mmol) in pyridine (16 mL) and dioxane (100 mL), and the solvent was evaporated. The residue was dissolved in CH2Cl2 (500 mL), washed with 5% aqueous NaHCO3 (3×100 mL), washed with brine (2×100 mL), dried over Na2SO4 and evaporated. The residue was purified on a silica gel column using a step gradient of ethyl acetate (0 to 15%) in toluene to give 1 (8.2 g, 67.5%) as an oil. HR MALDI MS: calculated for C31H36O9 (M+H+) 553.2442, found 553.2438. 1H NMR (CDCl3) δ 7.29 (6H, d, J=8.8 Hz), 6.83 (6H, d, J=8.8 Hz), 4.26-4.11 (6H, m), 3.80 (9H, s), 3.62 (2H, s), 2.11 (1H, t, J=5.8 Hz), 1.24 (6H, t, J=7.0 Hz). 13C NMR (CDCl3) δ 169.3 (C), 158.5 (C), 136.1 (C), 129.8 (CH), 113.2 (CH), 86.0 (C), 63.7 (CH2), 61.9 (CH2), 61.6 (CH2), 60.6 (C), 55.2 (CH3), 14.1 (CH3).

Provenance & Evidence