Dimethyl Sulfoxide → HCID 67782100, compound

Participants

Reaction Steps

Anhydrous 3-(N-pyrrolidinyl)propyltriphenylphosphonium bromide hydrobromide (47 g, 0.08 mole), 0.20 mole of n-butyl lithium in hexane (1.6 M), and 2,9-dibromo-6,11-dihydrodibenz[b,e]oxepin-11-one (25 g, 0.07 mole) in one liter of dry tetrahydrofuran by the procedure of Example 1, Step a. The crude product was chromatographed on a silica gel column (Waters Associates - Prep 500) with ethyl acetate/methanol (95:5) to give the product as 98% pure Z-isomer (0.30 g), mp 102°-103° C. pmr (DMSO-d6) δ: 7.31-7.54 (m, 5H, aromatic H), 6.79 (d, J=7.8 Hz, H4 of 98% Z), 6.67 (d, J=7.8 Hz, H of 2% E), 6.11 (t, CH= of 2% E), 5.78 (t, CH= of 98% Z), 2.34-2.56 (m, 8H, CH2 and 3NHCH2), 1.63 (m, 4H, 2CH2). And it gave another batch of the product as 90% pure E-isomer (0.18 g), mp 115°-116° C., pmr (DMSO) δ: 7.71-7.68 (m, 5H, aromatic H), 6.80 (d, J=7.8 Hz, H4 of 10% Z), 6.70 (d, J=7.8 Hz, H4 of 90% E), 6.10 (t, CH= of 90% E), 5.81 (t, CH= of 10% Z), 2.26-2.40 (m, 8H, CH2 and 3NCH2), 1.60 (m, 4H, 2CH2).

Provenance & Evidence