Reacción #49007

Ecuación de reacción

Diisopropyl azodicarboxylate

triphenylphosphine

N-hydroxyphthalimide

3-Methylsulfanyl-propan-1-ol

→

2-(3-methylsulfanyl-propoxy)-isoindole-1,3-dione

Rendimiento 65.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   Temperaturawith cooling the reaction vessel in an ice-bath under nitrogen atmosphere
3. 3
   workup.STIRRINGstirred for 5 hours
4. 4
   OtroAfter completion of the reaction
5. 5
   Concentraciónthe reaction mixture was concentrated under reduced pressure
6. 6
   Otrotriturated with diethyl ether:hexane (1:1, about 100 ml)
7. 7
   Otroto precipitate triphenylphosphine oxide as a white solid, which
8. 8
   Filtraciónwas filtered off
9. 9
   ConcentraciónThe filtrate was concentrated under reduced pressure
10. 10
    Otroto give a yellow oily residue
11. 11
    OtroThe resultant yellow oil was purified by silica gel flash chromatography (BW300, Fuji Silysia Chemical, 20% ethyl acetate/hexane as an eluent)

Procedimiento

3-Methylsulfanyl-propan-1-ol (4.133 g, 38.92 mmol) was dissolved in THF (anhydrous, 100 mL). To this solution, triphenylphosphine (10.2 g, 38.92 mmol) and N-hydroxyphthalimide (6.4 mg, 38.92 mmol) were added and dissolved with stirring. Diisopropyl azodicarboxylate (8.5 mL, 42.812 mmol) was added dropwise thereto with cooling the reaction vessel in an ice-bath under nitrogen atmosphere. The reaction mixture was warmed to room temperature, and stirred for 5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and triturated with diethyl ether:hexane (1:1, about 100 ml) to precipitate triphenylphosphine oxide as a white solid, which was filtered off. The filtrate was concentrated under reduced pressure to give a yellow oily residue. The resultant yellow oil was purified by silica gel flash chromatography (BW300, Fuji Silysia Chemical, 20% ethyl acetate/hexane as an eluent) to give 2-(3-methylsulfanyl-propoxy)-isoindole-1,3-dione (6.4 g, 65%).

Fuente