Tetrahydrofuran → HCID 86679331, compound

Participants

Reaction Steps

See Reaction Scheme 434 in FIG. 4E. A solution of 0.01 mole of 3-naphth-2-yl-2,5-dibromothiophene (prepared as described in Example 10) may be prepared in about 10 milliliters of anhydrous THF and cooled using a dry ice/acetone bath under an inert atmosphere. About 0.021 mole of n-butyllithium in hexane may be added, and the mixture may be stirred for about 30 minutes. Next, about 0.021 mole of 1-formyl piperidine may be added, and the mixture may be stirred and allowed to rise to room temperature over about 12 hours. The reaction mixture may be washed with aqueous ammonium chloride, and the organic layer may be dried and evaporated to form a residue. The residue may be purified via silica gel chromatography to give 3-(naphthalen-2-yl)thiophene-2,5-dicarbaldehyde.

Provenance & Evidence