4-Hydroxybenzaldehyde → HCID 56925554, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1-pentyn-3-ol 6 (0.319 mL, 2.83 mmol) in acetonitrile (3 mL) at 0° C. was added DBU (0.55 mL, 3.69 mmol). Then TFAA (0.34 mL, 2.46 mmol) was added drop wise and the solution was stirred at 0° C. for 30 min. To a solution of 4-hydroxybenzaldehyde (300 mg, 2.46 mmol) in acetonitrile at 0° C. was added DBU (0.55 mL 3.69 mmol) and CuCl2.2H2O (0.42 mg, 0.0025 mmol). The first mixture was added to the second mixture over a period of five min. The reaction was stirred overnight. The solvent was removed by rotary evaporation and the residue diluted with DCM. Then the organic layer washed with 1M HCl, 1M NaOH, sat NaHCO3 and brine, dried over MgSO4 and concentrated in vacuum to give 170 mg (32%) of product. 1H NMR (CDCl3): δ 9.91 (s, 1H), 7.83-7.81 (m, 2H), 7.36-7.34 (m, 2H), 2.69 (s, 1H), 2.06-1.92 (m, 2H), 1.66 (s, 3H), 1.12 ppm (t, J=7.2 Hz, 3H).

Provenance & Evidence