Triethylamine → (E)-N-benzyl-3-chloro-N-(2-methylbut-2-enyl)-1,2-dihydrocyclobutabenzene-1-carboxamide

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Reaction Steps

3-Chloro-1,2-dihydrocyclobutabenzene-1-carboxylic acid (3.78 mmol, 690 mg) was dissolved in DCM (10 ml). (E)-N-benzyl-2-methylbut-2-en-1-amine (5.67 mmol, 993 mg) and triethylamine (7.56 mmol, 1.050 ml, 765 mg) were added, followed by cyclophos 50% in ethyl acetate (4.53 mmol, 2.70 ml, 2886 mg). The reaction mixture was stirred overnight at room temperature and then diluted with DCM (5 ml) and washed in turn with 2 N HCl (10 ml), 2 N NaOH (10 ml) and brine (10 ml). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a crude residue that was purified by silica column chromatography (eluting with heptane—50% ethyl acetate:heptane) to give (E)-N-benzyl-3-chloro-N-(2-methylbut-2-enyl)-1,2-dihydrocyclobutabenzene-1-carboxamide (430 mg). m/z: 340.5 [M+H]+.

Provenance & Evidence