Dimethyl malonate → HCID 21265692, compound

Participants

Reaction Steps

To dimethyl malonate (6.60 g, 50 mmol) in DMF (100 mL) was added NaH (2.00 g, 50 mmol) and 4-bromomethyl bromobenzene (25 g, 100 mmol). After a period of 6 h at room temperature, 200 mL of saturated NH4Cl and 200 mL of H2O were added. The crude product was extracted with a mixture of toluene and ether, dried over Na2SO4, filtered and evaporated. To the oil dissolved in THF (300 mL) at 0° C. LAH (4.5 g) was added. After a period of 2 h at room temperature, the reaction was quenched with 20 mL of acetone and 300 mL of 20% potassium, sodium tartrate. The compound was extracted with EtOAc, dried over Na2SO4, evaporated and purified by flash chromatography to provide 19 g of material.

Provenance & Evidence