5-Iodo-1-oxo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl ester → 1-Ethyl-1-hydroxy-5-iodo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl ester

Participants

Reaction Steps

Into a glass vial containing the product from step (f) (170 mg, 0.409 mmol) dissolved in diethyl ether (4 ml), ethylmagnesium bromide (3M diethyl ether, 1.3 ml, 4.09 mmol) was added at reflux. The reaction mixture was stirred at reflux for 20 minutes. The reaction mixture was allowed to cool to room temperature and was then quenched with saturated aqueous NH4Cl (30 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give a yellow oil (197 mg) that was used without further purification. MS: ESI (positive): 446 (M+H).

Provenance & Evidence