Diethyl (cyanomethyl)phosphonate → 3-(Cyanomethylene)-1-(methoxymethyl)cyclobutanecarbonitrile

反応式

CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH3:18][O:19][CH2:20][C:21]1([C:26]#[N:27])[CH2:24][C:23](=O)[CH2:22]1>O1CCCC1>[C:7]([CH:9]=[C:23]1[CH2:24][C:21]([CH2:20][O:19][CH3:18])([C:26]#[N:27])[CH2:22]1)#[N:8]

参加物

実験手順

To a solution of 1.0000 M of potassium tert-butoxide in tetrahydrofuran (2.25 mL) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (0.381 mL, 0.00236 mol) in tetrahydrofuran (4 mL, 0.05 mol). The reaction was warmed to rt and then cooled to 0° C. again. To the reaction mixture was added a solution of 1-(methoxymethyl)-3-oxocyclobutanecarbonitrile (0.298 g, 0.00214 mol) in tetrahydrofuran (2 mL, 0.02 mol). The reaction was allowed to warm up to rt and stirred at rt overnight. After quenching with water, the mixture was extracted with ether. The combined organic layers were washed with water, brine, dried and evaporated to dryness. The crude mixture was used directly in next step. LCMS calculated for C9H11N2O(M+H)+: 163.1. Found: 163.1.