Reacción #461450

Ecuación de reacción

iodine

tributyl(iodomethyl)tin

(E,E)-Farnesol

→

pale yellow liquid

Rendimiento 108.3%

Tributyl[[(3,7,11-trimethyl-2,6,10-dodecatrienyl)oxy]methyl]tin

Rendimiento 108.3%

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoA 1.15 g (10.0 mmol) of 35% KH in mineral oil was washed with three 5 mL portions of dry hexane
2. 2
   Otroto give a white suspension
3. 3
   workup.WAITafter 75 minutes
4. 4
   workup.STIRRINGThe mixture was stirred for three hours
5. 5
   Otrocarefully quenched with methanol
6. 6
   LavadoUpon dilution with diethyl ether, the organic layer was washed with water and brine
7. 7
   Secadodried (MgSO4)
8. 8
   Otroevaporated

Procedimiento

A 1.15 g (10.0 mmol) of 35% KH in mineral oil was washed with three 5 mL portions of dry hexane and suspended in 15 mL of dry tetrahydrofuran (THF) under argon. A solution of 242 mg (0.95 mmol) of iodine in 10 mL of THF was added over 50 minutes and the reaction was allowed to stir for an additional 40 minutes at room temperature to give a white suspension. (E,E)-Farnesol (1.5 g, 6.75 mmol) in 10 mL of THF was added dropwise over 15 minutes, and after 75 minutes, a solution of 2.43 g (5.64 mmol) of tributyl(iodomethyl)tin was added rapidly in 6 mL of THF. The mixture was stirred for three hours and carefully quenched with methanol. Upon dilution with diethyl ether, the organic layer was washed with water and brine, dried (MgSO4) and evaporated to give 3.21 g of a pale yellow liquid. The crude material was chromatographed on 720 g of silica gel eluted with 0.5:99.5 diethyl ether: petroleum ether, and the impure fractions were further purified on 150 g of silica gel eluted with 0.33:99.67 diethyl ether:petroleum ether to provide a total of 2.09 g (71%) of pure title stannane as a colorless liquid.

Fuente