Silver trifluoroacetate → Tetrasilver (phenoxymethylene)-bisphosphonate

HRID 569619Notes

Reaction equation

HRID 569619 reaction equation
[O:1]([CH:8]([P:13](=[O:16])([OH:15])[OH:14])[P:9](=[O:12])([OH:11])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.[Ag+:24]>C(O)C>[O:1]([CH:8]([P:13](=[O:14])([O-:15])[O-:16])[P:9](=[O:10])([O-:11])[O-:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[Ag+:24].[Ag+:24].[Ag+:24].[Ag+:24]

Participants

4

Reactant 2

HCID 76299Silver trifluoroacetateHCID 9816823(Phenoxymethylene)-bisphosphonic acid

Product 1

HCID 86742064Tetrasilver (phenoxymethylene)-bisphosphonateYield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of (phenoxymethylene)-bisphosphonic acid (8.04 g) in absolute ethanol (50 ml) was added to a stirred solution of silver trifluoroacetate (33.15 g) in absolute ethanol (200 ml). The mixture was cooled in ice and filtered. Drying in vacuo gave tetrasilver (phenoxymethylene)-bisphosphonate as a beige powder (17.9 g) which was suspended in acetonitrile (360 ml) and treated with iodomethyl pivalate (31.1 g). After stirring for 30 minutes at room temperature, the mixture was filtered, and the filtrate was evaporated in vacuo to leave a crude oil which was purified by chromatography on silica gel to give the title compound as a colourless oil.

Workup

  1. temperatureThe mixture was cooled in ice
  2. filtrationfiltered
  3. customDrying in vacuo

Sources & evidence

ORD record
ord-86d879fe5ab344fe9c05ab81f3413a97
Source dataset
uspto-grants-1988_03
Patent number
US04732998

Reaction notes

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