Ethyl bromoacetate → HCID 12132636, compound

Participants

Reaction Steps

9-cyano-10,10-Dimethyl-9,10-dihydroanthracene [9] (0.8 g, 3.42 mmol) was added to sodium ethoxide prepared from Na metal (0.110 g, 4.80 mmol) and ethanol (10 mL) and heated under reflux for one hour leading to the development of a greenish brown solution. The solution was then cooled in an ice bath and ethyl bromoacetate (0.80 g, 4.80 mmol) was added dropwise via a syringe. The resulting mixture was then heated at reflux (4 h) and filtered. The solid 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, brine, dried (MgSO4) and evaporated under reduced pressure to give an oil which was purified by medium pressure liquid chromatography using pet. ether: EtOAc (9:1) as eluent to give 0.978 g (74%) of the product as a colorless oil. 1H NMR (CDCl3)d: 0.98-1.06 (t, 3H, CH3), 1.64-1.67 (d, J=9Hz, 3H, CH3), 1.71-1.74 (d, J=9 Hz, 3H, CH3), 3.04-3.07 (d, J=9Hz, 2H, CH2), 3.86-3.94 (q, 2H, CH2), 7.29-7.77 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 14.39, 33.85, 35.21, 38.37, 52.29, 61.38, 123.17, 127.53, 127.84, 128.17, 129.48, 130.97, 143.23, 167.97.

Provenance & Evidence