Ethyl bromoacetate → HCID 12132633, compound

Participants

Reaction Steps

9-Cyano-9,10-dihydroanthracene [2] (1.25 g, 6.09 mmol) was added to sodium ethoxide prepared from Na (0.196 g, 8.53 mmol) and EtOH (10 mL) and heated at reflux (1 hr). The solution was then cooled in an ice bath and ethyl bromoacetate (1.42 g, 8.53 mmol) was added drop wise via a syringe. The resulting mixture was heated at reflux (4 h) cooled and filtered. The residue was washed with ether (25 mL). Water (25 mL) was added to the filterate and the organic layer was separated. The aqueous layer was once again extracted with ether (25 mL). The combined ether extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure to give an oil which was purified by mplc using pet. ether: EtOAc (9:1) as eluent to give 1.245 g (70%) of the product as a colorless oil, which crystallized on prolonged standing: mp 69-70° C. (EtOAc-pet. ether). 1H NMR (CDCl3)d: 1.10-1.15 (t, J=7.5 Hz, CH3), 2.85 (s, 2H, CH2), 3.97-4.14 (m, 4H, CH2), 7.33-7.89 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 14.53, 35.27, 46.05, 46.28, 61.63, 121.89, 127.58, 127.70, 128.93, 134.21, 135.10, 167.96

Provenance & Evidence