Tetraethyl vinylidene phosphonate → HCID 86746979, compound

HRID 1588052Notes

Reaction equation

HRID 1588052 reaction equation
[CH2:1]([O:3][P:4]([C:9]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH2:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N+:19](=[CH:21][C:22](=[O:38])[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:27]([F:37])[CH:26]=1)[CH3:24])=[N-:20]>CCOCC>[CH2:16]([O:15][P:11]([C:9]1([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[CH2:10][C:21]([C:22](=[O:38])[CH:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:27]([F:37])[CH:26]=2)[CH3:24])=[N:19][NH:20]1)(=[O:18])[O:12][CH2:13][CH3:14])[CH3:17]

Participants

4

Reactant 2

HCID 11022954Tetraethyl vinylidene phosphonateHCID 54327081HCID 54327081, compound

Product 1

HCID 86746979HCID 86746979, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethenylidene bisphosphonic acid tetraethyl ester (II, PREPARATION 1, 11.1 g) and 1-diazo-3-[2-fluoro(1,1'-biphenyl)-4-yl]-butan-2-one (I, PREPARATION 3, 10.0 g) are stirred for 18 hrs in ether (40 ml). A seed crystal from an earlier reaction is added to the mixture, whereupon the reaction sets up into a solid mass. The precipitate is filtered, then recrystallized from methylene chloride/hexane (45/55) to give the title compound, mp 109°-110°; MS (m/e) 568, 431, 403, 385, 341, 313, 301 and 199; IR (mineral oil mull) 3179, 1656, 1557, 1265, 1246, 1033, 1009, 993, 976 and 965 cm-1 ; NMR (CDCl3) 7.4, 7.2, 6.91, 4.81, 4.4, 4.05, 3.4, 1.49, 1.34, 1.16 and 1.08 δ; CMR (CDCl3) 195.1, 162, 158, 149, 142, 136, 130.7, 128.8, 128.5, 127.6, 123.9, 115.8, 115.6, 64.3, 63.6, 46.1, 36.4, 17.7, 16.5, 16.2 and 16.1 δ.

Workup

  1. customA seed crystal from an earlier reaction
  2. additionis added to the mixture, whereupon the reaction
  3. filtrationThe precipitate is filtered
  4. customrecrystallized from methylene chloride/hexane (45/55)

Sources & evidence

ORD record
ord-547ac5fd24364d849546a534f0d5512c
Source dataset
uspto-grants-1993_06
Patent number
US05220021

Reaction notes

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