Reacción #1150598

Ecuación de reacción

potassium sodium tartaric acid

3-phenyl-2-propyn-1-ol

Red-Al

iodine monochloride

→

crude title compound

Rendimiento 95.0%

3-Iodo-3-phenyl-prop-2-en-1-ol

Rendimiento 95.0%

Disolventes

diethyl ether

toluene

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturato warm to room temperature
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   Otroproducing a white precipitate
5. 5
   Otrothis was removed by filtration
6. 6
   Extracciónthe filtrate was extracted with diethyl ether (3×75 ml)
7. 7
   LavadoThe combined organic extracts were washed with sodium thiosulphate (5×60 ml), brine
8. 8
   Secadodried (MgSO4)
9. 9
   Otrothe solvent removed in vacuo

Procedimiento

Red-Al™ (3.4M in toluene, 33 ml) was dissolved in diethyl ether (100 ml) and cooled to −10° C. to which 3-phenyl-2-propyn-1-ol (10 g, 0.076 mol) dissolved in diethyl ether (10 ml) was added dropwise, causing the solution to turn a dark red/brown colour. The reaction was stirred for 1 hour. The solution was cooled to −78° C. and iodine monochloride (1.0M solution in dichloromethane, 114 ml) was added causing the solution to turn a dark brown colour. The mixture was allowed to warm to room temperature and stirred for 1 hour. A 10% solution of potassium sodium tartaric acid (800 ml) was added, producing a white precipitate, this was removed by filtration and the filtrate was extracted with diethyl ether (3×75 ml). The combined organic extracts were washed with sodium thiosulphate (5×60 ml), brine, dried (MgSO4) and the solvent removed in vacuo to afford the crude title compound as a light brown oil (19.5 g, 95%).

Fuente