Hydrochloric Acid → Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

反応式

[C:1]1(=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:15]O.Cl>>[CH3:15][O:12][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][C:1]2=[O:14])=[CH:6][CH:7]=1)=[O:13]

参加物

反応物 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 147565478-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

生成物 1

HCID 10987358Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate収率 49%

実験手順

Part A--A mixture of 1-tetralon-7-carboxylic acid (7.0 g, 0.037 mol) in methanol (13.6 mL, 10.8 g, 0.30 mol) with a catalytic amount of hydrochloric acid (0.07 mL, 0.12 g, 0.0012 mol) was stirred at reflux over 5 hours. The cooled reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were backwashed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The resulting solid was purified by flash chromatography using hexane:ethyl acetate::75:25. The resulting solid was triturated with hexane to give 1-tetralon-7-carboxylic acid methyl ester (3.61 g, 0.018 mol, 49%) as a yellow solid. mp=170°-172° C.; 1H NMR (CDCl3) d 8.7 (s, 1H), 8.15 (d, 1H, J=8.1 Hz), 7.35 (d, 1H, J=8.1 Hz), 3.95 (s, 3H), 3.05 (d, 2H, J=6.1 Hz), 2.7 (t, 2H, J=6.4 Hz), 2.15 (quintet, 2H, J=6.2 Hz).