Potassium Hydroxide → [4-(Diazo-phenyl-methyl)-benzyl]phosphonic acid diethyl ester

Beteiligte Stoffe

Reaktionsschritte

To a mixture of mercury (II) oxide (0.21 g, 0.97 mmol), sodium sulphate (0.16 g, 1.1 mmol) and sat potassium hydroxide in ethanol (0.2 ml) was added a solution of 15 (0.28 g, 0.81 mmol) in dry THF (20 ml). The mixture was stirred in the dark for 1 h. the filtered through a celite pad. Concentration of the filtrate in vacuo yielded 16 (0.25 g, 89%) as a dark red oil; δH (CDCl3) 1.28 (6H, d, JH-H=7.1 Hz, 2×CH2CH3), 3.16 (2H, d, JH-P=21.7 Hz, ArCH2P), 3.98-4.13 (4H, m, 2×CH2CH3), 7.15-7.43 (9H, m, Ar—H) ppm; δC (CDCl3) 16.4 (d, JC-P=6.0 Hz, 2×CH2CH3), 33.3 (d, JC-P=138.2 Hz, ArCH2P), 62.1 (d, JC-P=6.8 Hz, 2×CH2CH3), 125.1, 125.2, 125.2, 125.6, 129.1 (Ar—C), 129.4 (4-C), 130.4 and 130.5 (1-, 1′-C) ppm; δP (CDCl3) 26.37 ppm; νmax (thin film) 2982 (C—Hst), 2039 (C═N=Nst), 1248 (P═Ost), 1027 (P—Ost) cm−1; m/z (ES+) 403 ([M+NH4+MeCN]+100%); found (FI+) 344.1778, C18H21N2O3P requires 344.1290.

Herkunft & Nachweise