6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester → 6-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

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Reaction Steps

10% Pd/C (195 mg) was added to a suspension of 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester (1.07 g, 4.32 mmol) and FeCl3, (5 mg) in EtOH (30 mL) under N2. The suspension was hydrogenated at 40 psi for 3 days. The suspension was filtered through a Celite pad and the filtrate was concentrated to a leave crude oil. The oil was purified using medium pressure chromatography on silica (CHCl3) to provide a colorless oil (886 mg, 88.3% yield). 1H-NMR (300 MHz, CDCl3) δ 1.28 (t, J=7.2 Hz, 3H). 1.84 (m, 1H), 2.19 (m, 1H), 2.70 (m, 1H), 2.83 (m, 2H), 2.93 (m, 2H), 3.77 (s, 3H), 4.17 (q, J=7.2 Hz, 2H), 6.62 (s, 1H), 6.69 (dd, J=8.4, 2.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H).

Provenance & Evidence