Benzenepropanoyl chloride → HCID 71549356, compound

Participants

Reaction Steps

To a 0° C. solution of compound 5 (0.2 g, 0.72 mmol) in THF (4 mL) was added Hunig's Base (0.09 g, 0.72 mmol) followed by hydrocinnamoyl chloride (0.12 g, 0.72 mmol) dropwise. The resulting mixture was allowed to stir overnight at room temperature, diluted with EtOAc and washed with satd. aq. NaHCO3, satd. aq. NaCl and dried over MgSO4. Purification by flash silica chromatography (MeOH/CH2Cl2) gave a yellow oil (0.12 g, 0.29 mmol, 41% yield). HPLC purity 98.4% (tR=5.02 min). NMR (500 MHz, CDCl3) δ 7.2 (s, 1H), 7.1-7.2 (m, 4H), 6.8-6.9 (m, 3H), 4.8 (s, 1H), 4.3 (s, 4H), 2.9 (s, 3H), 2.8-3.2 (m, 4H), 2.5-2.6 (m, 2H), 1.8-2.1 (m, 2H), 1.5-1.8 (m, 4H). ESI-MS m/z 425.1 (M+H+).

Provenance & Evidence