Potassium Carbonate → HCID 89690204, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-hydroxy-2-propyl-benzoate (40.0 g, 206 mmol) and 1-benzyloxy-5-(3-chloropropoxy)-4-ethyl-2-(4-fluorophenyl)benzene (prepared according to Org. Process Res. Dev. (2009), 13: 268-275) (82.15 g, 206 mmol) in dimethylsulfoxide (240 mL) add potassium carbonate (30.2 g, 219 mmol) and N,N-dimethylpyridin-4-amine (2.0 g, 16 mmol) in succession. Stir the suspension for 87 h at 60° C. and then allow it to cool. Dilute the mixture with water (600 mL) and with methyl-tert-butylether (100 mL) and stir for 15 min. Separate the phases and wash the aqueous portion with methyl-tert-butylether (3×30 mL). Wash the combined organic extracts with water and brine. Concentrate the organic portion in vacuo to yield the title compound (123.0 g, quantitative) as a brown oil. ES/MS m/z 557 (M+1).

Provenance & Evidence