Reaction #2787

Reaction equation

water

imidazole

methyl 1-dimethoxyphosphinylethenesulfonate

bromotrimethylsilane

→

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

Solvents

chloroform

Conditions

Workup

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

Procedure

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.

Source