Reaction #214959

Reaction equation

2,4-dimethyl-3-hydroxymethyl-5-(methylthio)thiophene

triphenylphosphonium bromide

ethyl acetate

acetonitrile

→

[2,4-dimethyl-5-(methylthio)-3-thenyl]triphenylphosphonium bromide

Solvents

ethyl ether hexane

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was cooled
2. 2
   workup.ADDITIONpoured into 150 ml
3. 3
   OtherThe resulting solution was decanted from a gum-like residue
4. 4
   workup.ADDITIONThe residue was treated with hot acetone
5. 5
   Filtrationthe resulting white crystals were filtered
6. 6
   Washwashed with cold acetone
7. 7
   Otherdried under high vacuum at 80° C.

Procedure

14.0 G. of 2,4-dimethyl-3-hydroxymethyl-5-(methylthio)thiophene and 26.0 G. of triphenylphosphonium bromide were dissolved in 75 ml. of acetonitrile and stirred at 40° C. for 1 hour. The resulting mixture was cooled and poured into 150 ml. of ethyl acetate then treated with ethyl ether/hexane (5:1). The resulting solution was decanted from a gum-like residue. The residue was treated with hot acetone and the resulting white crystals were filtered, washed with cold acetone and dried under high vacuum at 80° C. to yield [2,4-dimethyl-5-(methylthio)-3-thenyl]triphenylphosphonium bromide, m.p. 245°-248° C.

Source