Sodium hydride → Tert-butyl 1-bromo-7-cyano-2-naphthyl(3-chloro-2-propen-1-yl)carbamate

참여 물질

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A solution of 194 (2.50 g, 7.21 mmol) in DMF (20 mL) was added to a suspension of NaH (350 mg, 8.65 mmol, 60% in oil) in DMF (20 mL) at 0° C. 1,3-Dichloropropene (1.60 g, 14 mmol) was added and the mixture was allowed to warm to room temperature over 2 h. The DMF was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with water (×2), brine (×2) and dried. Filtration through silica gel gave tert-butyl 1-bromo-7-cyano-2-naphthyl(3-chloro-2-propen-1-yl)carbamate (195) (3.28 g, 100%) as a pale yellow oil; 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 8.73 (s, 1H), 7.93-7.96 (m, 1H), 7.83-7.87 (m, 1H, 7.68-7.70 (m, 1H), 7.39-7.46 (m, 1H), 6.00-6.11 (m, 2 H), 4.49-4.62 (m, 1H), 4.33-4.43 (m, 1H), 1.33, 1.32 (2's, 9 W. HRMS (FAB) calcd. for C19H1879Br35ClN2O2 (MH+) m/z 421.0318, found 421.0330.

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