Tetraethyl vinylidene phosphonate → HCID 10026850, compound

HRID 1588051Notes

Reaction equation

HRID 1588051 reaction equation
[CH:1]1([C:7](=[O:11])[CH:8]=[N+:9]=[N-:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]([O:14][P:15]([C:20]([P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH2:21])(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13]>CCOCC>[CH2:24]([O:23][P:22]([C:20]1([P:15](=[O:19])([O:14][CH2:12][CH3:13])[O:16][CH2:17][CH3:18])[CH2:21][C:8]([C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:11])=[N:9][NH:10]1)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:25]

Participants

4

Reactant 2

HCID 11022954Tetraethyl vinylidene phosphonateHCID 53903884HCID 53903884, compound

Product 1

HCID 10026850HCID 10026850, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Cyclohexyl-2-diazoethanone (I, PREPARATION 2, 3.1 g) and ethenylidene bisphosphonic acid tetraethyl ester (II, PREPARATION 1, 6.00 g) are stirred in ether (20 ml) for 24 hrs at 22°. The precipitate is filtered, washed with ether, then recrystallized from ethyl acetate to give the title compound, mp 166°-165°; MS (m/e) 452, 341, 315, 287, 259, 241, 223 and 205; IR (mineral oil mull) 3186, 1656, 1552, 1449, 1267, 1253, 1241, 1162, 1041, 1019, 995 and 969 cm-1 ; NMR (CDCl3) 6.77, 4.24, 3.45, 3.24 and 1.9-1.2 δ.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with ether
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e5caa12a15b540298f03ced9727bafaf
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

Loading…