7-Bromo-4-methoxy-1H-indene-2,3-dicarboxylic acid, diethyl ester → 4-Methoxy-2,3-dihydro-1H-indene-2,3-dicarboxylic acid, diethyl ester

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Reaction Steps

The diester from Example 2 (19.39 g) was dissolved in 250 ml ethanol. To the solution was added 5.20 g of 10% Pd/BaSO4 and 7.15 g NaOAc.3H2O. The reaction was hydrogenated at 4 atm pressure. The catalyst was filtered and the solvent evaporated. The product was dissolved in ether, washed with 5% NaHCO3, dried (MgSO4), and the solvent was evaporated to yield 14.87 g of the desired product as a colorless oil. NMR (CDCl3) δ1.20 (t, 3H), 1.27 (t, 3H), 3.13 (dd, 1H), 3.48-3.56 (m, 2H), 3.82 (s, 3H), 3.95-4.22 (m, 4H), 4.39 (d, 1H), 6.70 (d, 1H), 6.87 (d, 1H), 7.21 (t, 1H).

Provenance & Evidence