3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 19707442, compound

Participants

Reaction Steps

To a suspension of 3-cyclopentyloxy-4-methoxybenzaldehyde (6.07 g, 27.6 mmol) and diphenyl 1-chloro-1-(4-pyridyl)methanephosphonate (J. Org. Chem., 1992, 57, 1622) (9.03 g, 52.1 mmol) in dioxane (150 mL) there was added in portions potassium tert-butoxide (7.03 g, 62.8 mmol). The mixture was stirred at room temperature for 1 h and then refluxed. After 3.5 h, there was added another 7 g of potassium tert-butoxide and refluxing was continued for 18 h. After cooling, the mixture was diluted with water (1 L) and extracted 3 times with EtOAc. The extracts were washed 3 times with water, dried and evaporated and the residue was chromatographed on silica gel (EtOAc/hexane 1:2) to afford the title acetylene (4.72 g, 64%) as a cream-colored solid.

Provenance & Evidence