8,9-Dihydro-5H-benzo[7]annulen-7(6H)-one

Preparation 3 6 M HCl was added to a solution of diester 10 (100.4 mg, 0.37 mmol, 1 equiv) dissolved in CHB. The crude dimethyl 7-oxo-6, 7, 8, 9-tetrahydro-5H-benzo[7]annulene-6, 8- dicarboxylate was dissolved in 200 mL of ethanol (EtOH) and then 100 mL of 2 N KOH. The resulting mixture was refluxed at 85 B. The crude dimethyl 7-oxo-6, 7, 8, 9-tetrahydro-5/-/-benzo[7]annulene-6, 8- dicarboxylate was dissolved in 200 mL of ethanol (EtOH) and then 100 mL of 2 N KOH. The resulting mixture was refluxed at 85 Sodium hydride (60percent in mineral oil, 1.2 g, 29.9 mmol) and a catalytic amount of tert-butanol were combined in toluene (100 mL). The solution was brought to reflux and a solution of E54A (10 g, 29.9 mmol) in toluene (30 mL) was added dropwise overnight while maintaining the solution at reflux. After cooling the reaction to room temperature, glacial acetic acid (4 mL) was added dropwise followed by rapid addition of ice water. The layers were separated. The organic layer washed with brine (2.x.) and water (2.x.); dried over sodium sulfate; filtered; and concentrated. The crude residue was added to a mixture of methanol (70 mL) and 6 N hydrochloric acid (30 mL) and heated at reflux for 3 h. After cooling to room temperature, the solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2.x.) and brine (2.x.); dried over sodium sulfate; and concentrated. Column chromatography of the residue on silica gel (10percent ethyl acetate/hexanes) afforded 2.5 g (52percent) of E54B.

Molecular Weight:160.21
XLogP3:1.9
Hydrogen Bond Acceptor Count:1
Exact Mass:160.088815002
Monoisotopic Mass:160.088815002
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes