Sodium hydride → 2-(3,5-Difluoro-2-nitro-phenyl)-malonic acid di-tert-butyl ester

反応式

[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].F[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[C:20]=1[N+:27]([O-:29])=[O:28]>CN(C=O)C>[C:14]([O:13][C:3](=[O:12])[CH:4]([C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[C:20]=1[N+:27]([O-:29])=[O:28])[C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])([CH3:17])([CH3:16])[CH3:15]

参加物

実験手順

To a suspension of NaH (54.6 g, 60%, 1.365 mol) in 600 mL of DMF was added di-t-Butyl malonate (118 g, 0.546 mol) at 0° C. and stirred for 30 min. 2,4,6 trifluoronitrobenzene was added as a solution in 400 mL of DMF (75 g, 0.42 mol) over 3 hours and the solution stirred at ambient temperature for 12 hours. The reaction mixture was extracted with ethyl acetate (3×'s). The ethyl acetate was washed with water (3×'s) and with brine and dried over MgSO4 and concentrated to give 62 g of crude product. LCMS [M+Na]—396; 1H NMR (500 MHz, DMSO) δ 7.81 (m, 1H), 7.27 (m, 1H), 5.00 (s, 1H), 1.41 (m, 18H).