Tetraethyl vinylidene phosphonate → HCID 10000902, compound

HRID 1588055Notes

Reaction equation

HRID 1588055 reaction equation
[N+:1](=[CH:3][C:4](=[O:7])[CH2:5][CH3:6])=[N-:2].[CH2:8]([O:10][P:11]([C:16]([P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH2:17])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9]>CCOCC>[CH2:20]([O:19][P:18]([C:16]1([P:11](=[O:15])([O:10][CH2:8][CH3:9])[O:12][CH2:13][CH3:14])[CH2:17][C:3]([C:4](=[O:7])[CH2:5][CH3:6])=[N:1][NH:2]1)(=[O:25])[O:22][CH2:23][CH3:24])[CH3:21]

Participants

4

Reactant 2

HCID 11022954Tetraethyl vinylidene phosphonateHCID 541882796831-84-1

Product 1

HCID 10000902HCID 10000902, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Diazo-2-butanone (I, PREPARATION 4, 3.1 g) in ether (50 ml) is treated with ethenylidene bisphosphonic acid tetraethyl ester (II, PREPARATION 1, 9.5 g), stirred at 20°-25° overnight, and concentrated. The concentrate is crystallized twice from methylene chloride/SSB to give the title compound, mp 96°-98°; MS (m/e) 398, 261, 233 and 205; IR (mineral oil mull) 3210, 0664, 1265, 1245, 1046, 1024, 997 and 983 cm-1 ; NMR (CDCl3) 6.92, 4.14-4.33, 3.48, 2.82, 1.30-1.36 and 1.12 δ; CMR (CDCl3) 196, 149, 66, 64, 36, 31, 16 and 8 δ.

Workup

  1. concentrationconcentrated
  2. customThe concentrate is crystallized twice from methylene chloride/SSB

Sources & evidence

ORD record
ord-1c31b2bb548c4f0ea53f7db43a893d2d
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

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