반응 단계
To solution of 9 (1.09 g, 43 mmol) in methanol (10 ml) was added hydrazine hydrate (1.08 g 20 mmol). The mixture was heated to reflux for 48 h. then concentrated in vacuo. The residue was partioned between DCM and water and the organic layer collected and concentrated to yield 10 (1.10 g, 98%) as a mixture of cis and trans isomers and as a yellow oil; δH (CDCl3) 4.03, 4.13 (2×dt, 2H, J=1.4, 5.6 Hz, OCH2CH═CH2) 4.52, 4.60 (2×s, 2H, ArCH2O), 5.20, 5.27 (ddd, 1H, J=1.4, 3.0, 10.4 Hz, OCH2CH═CHH), 5.32, 5.37 (ddd, 1H, J=1.4, 3.2, 17.3 Hz, OCH2CH═CHH), 5.45 (bs, 2H, NNH2), 5.91-6.06 (m, 1H, OCH2CH═CH2), 7.28-7.31 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.46-7.55 (m, 5H, 2-, 2′-, 4′-, 6-, 6′-H) ppm; δC (CDCl3) 60.1, 71.5, 71.7 (ArCH2O, OCH2CH═CH2), 117.0, 117.3 (OCH2CH═CH2), 126.3, 126.4, 127.4, 128.0, 128.5, 128.7, 129.3 (Ar—C), 134.4, 134.6 (2×OCH2CH═CH2), 137.7, 138.1, 139.1 (Ar—C), 148.7 (C═N) ppm; νmax (thin film) 3404, 3289, 3057, 2855, 1612, 1444, 1411, 1277, 1083 cm−1; m/z (ES+) 267 ([M+H]+, 100%); found (EST+) 267.1492, C17H19N2O requires 267.1492.
