Sodium hydride → (Z)-4-(2-(naphthalen-1-yl)vinyl)-1-(pentan-2-yl)-1H-indole

Participants

Reaction Steps

To a suspension of 95% sodium hydride (NaH, 347 mg, 13.76 mmol) in dimethyl ether (DME, 17 mL) was added diethyl(naphthalen-1-ylmethyl)phosphonate (4) (960 mg, 3.44 mmol) dropwise at 0° C. The resulting solution was stirred at room temperature for 1 h, then semi-pure 1-(pentan-2-yl)-1H-indole-4-carbaldehyde (3) (˜3.44 mmol) in DME (2 mL) was added dropwise and the reaction mixture was stirred for 8 h at room temperature. After the reaction completed as indicated by thin layer chromatography, the reaction mixture was poured into ice-cold water (30 mL), extracted with ethyl acetate (3×30 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (6:1 hexane/ethyl acetate) gave (Z)-4-(2-(naphthalen-1-yl)vinyl)-1-(pentan-2-yl)-1H-indole (5) (580 mg, 1.70 mmol) in 50% yield. 1H NMR (CDCl3): 8.30 (d, 1H, J=8.0 Hz), 8.09 (d, 1H, J=16.0 Hz), 7.91 (dd, 1H, J=7.5, 1.5 Hz), 7.86 (d, 1H, J=7.0 Hz), 7.84 (d, 1H, J=8.0 Hz), 7.59 (d, 1H, J=16.0 Hz), 7.58-7.52 (m, 3H), 7.48 (d, 1H, J=7.0 Hz), 7.39 (d, 1H, J=8.0 Hz), 7.32 (d, 1H, J=3.5 Hz), 7.29 (d, 1H, J=7.5 Hz), 6.91 (d, 1H, J=3.0 Hz), 4.61-4.53 (m, 1H), 2.00-1.92 (m, 1H), 1.88-1.80 (m, 1H), 1.56 (d, 3H, J=7.0 Hz), 1.36-1.20 (m, 4H), 0.93 (t, 3H, J=7.5 Hz).

Provenance & Evidence