HCID 17756178, compound → HCID 17755958, compound

Participants

Reaction Steps

To a solution of 2-[4-(4-hydroxy-but-1-ynyl)-benzyl]-isoindole-1,3-dione (2.0 g, 6.55 mmol) in ethanol/ethyl acetate (3:1, 163 mL) was added palladium on carbon (10 wt. %, 1.04 g). The reaction stirred at room temperature overnight under 50 psi of hydrogen. The reaction was monitored by 1H NMR to see conversion to product. Upon completion, the reaction mixture was filtered through diatomaceous earth (Celite®), washed with ethyl acetate, and concentrated to obtain the product as a yellow oil (1.88 g, 93% yield). 1H NMR (600 MHz, CDCl3): δ 7.81 (2H, m), 7.67 (m, 2H), 7.33 (d, 2H, J=8.1 Hz), 7.10 (d, 2H, J=8.1 Hz), 4.79 (s, 2H), 3.69 (q, 3H, J=7.0 Hz), 3.60 (t, 2H, J=6.5 Hz), 2.58 (t, 2H, J=7.4 Hz), 1.64 (m, 2H), 1.55 (m, 2H); 13C NMR (150 MHz, CDCl3): 168.3, 142.2, 134.1, 134.0, 132.3, 128.8, 128.8, 123.5, 62.9, 41.5, 35.4, 32.4, 27.6.

Provenance & Evidence