1,8-Diazabicyclo(5.4.0)undec-7-ene → E-4-Pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-one

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Reaction Steps

2 g (7.93 mmol) of dimethyl 2-oxo-3-pentyloxypropanephosphonate, 1.7 g (9.13 mmol) of 4-(1-imidazolylmethyl)benzaldehyde and 1.33 g (8.74 mmol) of DBU were stirred in 150 ml of dimethoxyethane at room temperature for 31 h. The mixture was filtered through silica gel and the solvent was removed from the filtrate in vacuo. Chromatography on silica gel (chloroform/methanol/25% aqueous NH3 =20/1/0.2) produced 1.5 g (4.80 mmol, 60%) as a yellowish oil which solidified in the refrigerator, melting point 35°-36° C.

Provenance & Evidence