Dimethyl malonate → HCID 86705577, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl malonate (6.155 ml, 53.72 mmol), (S)-ethyl 4-iodo-2-(triethylsilyloxy)butanoate (10.00 g, 26.86 mmol) and THF (100 mL), dimethyl malonate, (S)-ethyl 4-iodo-2-(triethylsilyloxy)butanoate (10.00 g, 26.86 mmol) was cooled to −78° C. and maintained under N2. To the solution was added sodium hydride (2.149 g, 53.72 mmol, 60% dispersion in mineral oil) portion wise over 5 min and the resulting mixture stirred at −78° C. for 3 h. The reaction was warmed to RT and stirred for 48 h. The reaction was quenched by adding H2O and extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (4:1) to afford 4.2 g, (41%) of (S)-4-ethyl 1,1-dimethyl 4-(triethylsilyloxy)butane-1,1,4-tricarboxylate (398).

Provenance & Evidence