Water → ethyl [(1S)-5-(2,2-diethoxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate

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Reaction Steps

To a solution of ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 1.55 g, 7.04 mmol) and bromoacetaldehyde diethyl acetal (4.85 g, 24.6 mmol) in DMF (10 mL) was added Cs2CO3 (2.75 g, 8.44 mmol) followed by water (5 mL). The reaction mixture was heated to reflux for 5 h, cooled to rt, and stirred for 18 h. The solvents were then evaporated under reduced pressure and the residue was dissolved in EtOAc. The organic solution was washed with water, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to afford the product (1.62 g, 68%) containing minor impurities. 1H NMR (400 MHz, CDCl3) δ 1.21-1.29 (m, 9H) 1.72-1.78 (m, 1H), 2.35-2.48 (m, 2H), 2.74-2.89 (m, 3H), 3.53-3.78 (m, 7H), 4.16 (d, 2H), 4.69 (t, 1H), 6.71 (d, 1H), 6.78 (s, 1H) 7.05 (d, 1H).

Provenance & Evidence