Sodium hydride → HCID 66966841, compound

Participants

Reaction Steps

To a solution of the compound of Step 4 (0.35 g, 1.6 mmol) in DMF (20 mL) at 0° C. was added NaH (1.2 eq.). After a period of 5 min., were added nBu4NI (0.10 g) and ethyl 4-bromobutyrate (0.40 mL). After a period of 1 h at room temperature, the reaction mixture was poured over saturated NH4Cl and EtOAc. The organic phase was separated, washed with H2O and dried over NaSO4. After evaporation the crude product was purified by flash chromatography. The bis ester was then dissolved in THF (7.0 mL) and a 1.06 M of THF solution of potassium tert-butoxide (2.2 mL) was added at 0° C. After a period of 1 h at room temperature, the reaction mixture was then poured over saturated NH4Cl and EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated under reduced pressure to provide the title compound as a mixture of ethyl and methyl ester.

Provenance & Evidence