反应详情

温度

130 °C

2-Pyridine carboxaldehyde (0.202 g, 1.9 mmol) was added to a mixture of 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (1) (0.322 g, 1.2 mmol) in piperidine:acetic acid (30 μL:24 μL). The reaction mixture was heated in a 130° C. oil bath with efficient stirring for 1.5 hours. After cooling to room temperature, 2 mL of 1N HCl was added and the mixture stirred overnight. The mixture was made neutral with the addition of a saturated solution of NaHCO3 and then extracted into DCM (3×50 mL). The pooled extracts were washed sequentially several times with water, then brine, dried, filtered, and concentrated in vacuo to leave a dark brown oil. Purification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM) afforded 0.075 g of the title compound as a light tan solid.

1. temperatureAfter cooling to room temperature
2. stirringthe mixture stirred overnight
3. extractionextracted into DCM (3×50 mL)
4. washThe pooled extracts were washed sequentially several times with water
5. dry with materialbrine, dried
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto leave a dark brown oil
9. customPurification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM)