1,3-Cyclohexadiene → HCID 10236664, compound

Participants

Reaction Steps

A solution of 104 (0.13 g, 0.32 mmol) in MeOH (10 mL) was treated with 0.2 g 10% Pd/C and cyclohexadiene (1 mL) and stirred at rt for 24 h. The reaction was filtered through a bed of Celite, concentrated and chromatographed on silica gel (1:1 EtOAc/hexanes) and the product was obtained as an oil which crystallized upon addition of CH2Cl2 to yield 48 mg of yellowish needles: Mp=238-239° C.; 1H NMR (DMSO-d6) δ 9.87 (brs, 1 H), 9.54 (brs, 1 H), 9.08 (br s, 1 H), 7.64 (d, 1 H, J=8.5 Hz), 7.21 (d, 1H, J=8.7 Hz), 7.05 (d, 2 H, J=8.4 Hz), 6.84 (dd, 1 H, J=8.5 Hz, 2.5 Hz), 6.76 (d, 2 H, J=8.5 Hz), 6.69 (dd, 2 H, J=6.6 Hz, 2.4 Hz), 6.63 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 5.84 (s, 1H); MS 317 (M−H)−.

Provenance & Evidence