Dimethylformamide → HCID 19010432, compound

Participants

Reaction Steps

Under N2, a suspension of 60% NaH (20 g, 0.5 mol), DMF (350 ml) and 7 (38.3 g, 0.13 mol) was stirred at ambient temperature. After 2.5 h. the reaction was cooled to 0°-4° C. and 2-methoxyethylbromide (71 g, 0.51 mol) was added dropwise. After complete addition, the reaction was allowed to stir to room temperature overnight. The solution was then poured into H2O and the aqueous layer was extracted with EtOAc (3x). The organic layer was washed with saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column with silica gel and the product eluted with 20% EtOAc-hexane to yield 39 g (84%) of 8.

Provenance & Evidence