Ethyl Acetate → 2-(2,3-dihydro-1H-inden-2-yl)ethanol

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A solution of ester 148 (68.8 g, 337 mmol) in dry THF (250 mL) was added to dropwise to a suspension of LiAlH4 (20.0 g, 501 mmol) in dry THF (500 mL) at 0° C. and the resulting mixture was stirred for 1.5 h. EtOAc was added to quench excess LiAlH4 and then aqueous H2SO4 solution (10%, 1 L) was added and the organic fraction separated. The aqueous solution was extracted with EtOAc (3×250 mL), and the combined organic fraction dried and the solvent evaporated to give alcohol 149 (54.5 g, 100%) (lit. Tanaka, et. al., J. Med. Chem. 1994, 37, 2071-2078) as a yellow oil: 1H NMR δ 7.16-7.25 (m, 2H, Harom), 7.09-7.14 (m, 2H, Harom), 3.74 (t, J=6.8 Hz, 2H, CH2O), 3.03-3.10 (m, 2H, CH2), 2.53-2.66 (m, 3H, CH2, CH), 1.82 (q, J=6.8 Hz, 2H, CH2), OH not observed.

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