Reaktion #2787

Reaktionsgleichung

water

imidazole

methyl 1-dimethoxyphosphinylethenesulfonate

bromotrimethylsilane

→

2-(1-imidazolyl)-1-phosphonoethanesulfonic acid

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred for about 30 minutes
2. 2
   Sonstigethe layers are separated
3. 3
   ExtraktionThe water layer is extracted several times with CHCl3 (extracts are discarded)
4. 4
   Sonstigeis evaporated to dryness under vacuum
5. 5
   SonstigeThe residue is triturated with acetone
6. 6
   Sonstigeto give a solid, which
7. 7
   Filtrationis collected by filtration
8. 8
   Sonstigerecrystallized from water/acetone

Vorschrift

A mixture of 0.68 g (0.01 mole) of imidazole and 2.30 g (0.01 mole) of methyl 1-dimethoxyphosphinylethenesulfonate (U.S. Pat. No. 5,011,938 issued to Barnett et al. on Apr. 30, 1991) in 20 ml of chloroform is stirred at 20°-50° for one day. The reaction is cooled to room temperature, and 10.7 g (0.07 mole) of bromotrimethylsilane is added. The mixture is stirred at 20°-30° for 2-3 days, and to it is then added 20 ml water. The mixture is stirred for about 30 minutes, and the layers are separated. The water layer is extracted several times with CHCl3 (extracts are discarded) and is evaporated to dryness under vacuum. The residue is triturated with acetone to give a solid, which is collected by filtration and recrystallized from water/acetone to afford 2-(1-imidazolyl)-1-phosphonoethanesulfonic acid.

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