Hydrochloric Acid → HCID 178430942, compound

Participants

Reaction Conditions

Reaction Steps

The product of step A (9 g, 46.8 mmol), NaOMe (16.0 mL, 70.2 mmol, 25% wt in MeOH) and diethyl ethoxymethylenemalonate (9.55 mL, 46.8 mmol) was dissolved in EtOH (100 mL). The reaction was heated for 1 h at 78° C. and became very thick. The mixture was slightly cooled and KOH (5.25 g, 94 mmol, 4.5 M in water) was added and the reaction became a cake. EtOH (20 mL) was added and the reaction was reheated at 78° C. for 90 min. Additional KOH (0.88 g, 15.7 mmol, 1 M in water) and EtOH (15 mL) were added and the reaction was heated 1 h. The mixture was cooled and HCl (20.9 mL, 265 mmol, 12 N) was added slowly and the slurry was diluted with Et2O. The solids were filtered, suspended in HCl (0.6 M) and re-filtered. The product was washed with Et2O:EtOH (1:1) and then hexane affording the titled compound. HPLC/MS: 221.1 (M+1); Rt=1.41 min.

Provenance & Evidence