Ethyl Acetate → HCID 15200028, compound

Participants

Reaction Steps

28.7 ml of boron tribromide solution (1M in dichloromethane) were added dropwise under argon and while cooling with ice to a solution of 1.95 g (5.75 mmol) of methyl (S)-2-benzamido-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylate in 15 ml of dichloromethane. The reaction mixture was stirred at 0° for 30 minutes and at room temperature for 3 hours and then poured into a mixture of ice, saturated ammonium chloride solution and ethyl acetate. The organic phase was separated, extracted with saturated sodium chloride solution, dried over MgSO4 and concentrated. The residue was dried in a high vacuum, suspended in diethyl ether/hexane (1:4) and filtered off. The filter residue was dried, there being obtained 1.75 g (97.8%) of (S)-2-benzamido-8-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid. [α]D =+84.3° (c=0.3, methanol). IR(KBr): 3362m(br.), 3064w, 3022w, 2976w, 2938w, 2620w, 1718s, 1644s, 1588m, 1523s, 1487m, 1467s, 1330m, 1278s, 1082w, 716m.

Provenance & Evidence