Tetrahydrofuran → (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one

Participants

Reaction Conditions

Reaction Steps

A 100 mL three-necked flask was charged with (S)-3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-ol (1.9 g, 6.13 mmol), anhydrous THF (40 mL), Et3N (2.0 mL, 14.4 mmol) and Pd(dppe)Cl2 (130 mg, 0.227 mmol) under nitrogen. The mixture was warmed to 40° C. and after 6 h, cooled to room temperature, diluted with EtOAc/hexane solution (1:3, 60 mL) and filtered through SiO2. The filtrate was concentrated in vacuo affording (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one as a yellow solid (1.85 g, 95%, 94% e.e.); mp 63.0-65.0° C.; Chiralpak AD column (93:7 IPA/hexane, 1 mL/min, 254 nm): 14.107 min (90.11%), 15.805 min (2.90%).1H NMR δ 7.25-7.1 (m, 3 H), 6.75 (d, J=7.9 Hz, 1 H), 6.6 (dd, J=1.7, 8.0 Hz, 1 H), 6.5 (d, J=1.7 Hz, 1 H), 5.9 (s, 2 H), 4.4 (dd, J=3.5, 7.8 Hz, 1 H), 3.95 (t, J=6.5 Hz, 2 H), 3.2 (dd, J=7.8, 19.3 Hz, 1 H), 2.6 (dd, J=3.5, 19.1 Hz, 1 H), 1.8 (quintet, J=7.8 Hz, 2 H), 1.01 (t, J=7.4 Hz, 3 H).

Provenance & Evidence