Pyridine → HCID 11207432, compound

Participants

Reaction Steps

Benzyl 2,2-bis(methylol)propionate (BnMPA) (11.2 g, 0.05 mol) was dissolved in CH2Cl2 (150 mL) and pyridine (25 mL, 0.3 mol) and the solution was chilled to −75° C. with dry ice/acetone under N2 atmosphere. A solution of triphosgene (7.5 g, 25 mmol) in CH2Cl2 (150 mL) was added dropwise over 1 hours, and then the reaction mixture was allowed to warm to room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl (75 mL), after which the organic layer was washed with 1 M aqueous HCl (3×100 mL), saturated aqueous NaHCO3 (1×100 mL), dried over MgSO4, filtered and evaporated. The resulting solid was recrystallized from ethyl acetate (15 mL) to give MTCOBn as a white solid (10.7 g, 86%). 1H NMR (400 MHz, CDCl3, 22° C.): delta 7.37 (m, 5H, PhH), 5.20 (s, 2H, —OCH2Ph), 4.69 (d, 2H, —CH2OCOO), 4.23 (d, 2H, —CH2OCOO), 1.31 (s, 3H, —CH3).

Provenance & Evidence