Dimethyl 2-methyl-2-(4-nitrophenyl)malonate → 2-Methyl-2-(4-nitrophenyl)-1,3-propanediol

Participants

Reaction Steps

To a stirred solution of dimethyl 2-methyl-2-(4-nitrophenyl)malonate (5 g, 18.72 mmol, 1.0 eq) in methanol (50 mL) was added NaBH4 (2.12 g, 56.17 mmol, 3.0 eq) at 0° C. and stirred at RT for 16 h. The solvent was evaporated and the residue was diluted with water (50 mL). The product was extracted with EtOAc (2×60 mL). The combined organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4, evaporated under reduced pressure. The crude product obtained was purified by CC using EtOAc/PE (1:1) to get 2-methyl-2-(4-nitrophenyl)propane-1,3-diol (1.6 g 40%; TLC system: EtOAc/PE (1:1), Rf: 0.2).

Provenance & Evidence