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

HRID 40455

Reaktionsgleichung

Reaktionsgleichung von HRID 40455
S([O-])([O-])(=O)=O.[Na+].[Na+].[OH-].[K+].[CH2:10]([O:12][P:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[N:32][NH2:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11]>C(O)C.C1COCC1.[Hg]=O>[CH2:10]([O:12][P:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[N+:32]=[N-:33])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11]

Komponenten

7

Edukt 3

HCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 86639978[4-(Hydrazono-phenyl-methyl)-benzyl]phosphonic acid diethyl ester

Produkt 1

HCID 86639977[4-(Diazo-phenyl-methyl)-benzyl]phosphonic acid diethyl esterAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30856Mercuric oxideKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationfiltered through a celite pad

Quellen und Nachweise

ORD-Eintrag
ord-4acf35f9643741958369dae75cf014a2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530212B2

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