Reacción #3994

Ecuación de reacción

2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate

sodium thiophenoxide

→

desired product

1-Phenylmercapto-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene

Disolventes

THF

HMPA

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe solution is washed with saturated aqueous NH4Cl and water
2. 2
   Otrodried
3. 3
   Otroannd evaporated in vacuo
4. 4
   Otroto give an oil
5. 5
   OtroPurification on a silica gel
6. 6
   Otrodry column

Procedimiento

To a solution of 1.85 g (5 mmol) of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate in 25 ml of anhydrous THF and 8 ml of HMPA is added in portions 0.68 g (5.2 mmol) of sodium thiophenoxide. The resulting mixture is stirred at room temperature for 18 hours and then taken up in 250 ml of diethyl ether. The solution is washed with saturated aqueous NH4Cl and water, dried annd evaporated in vacuo to give an oil. Purification on a silica gel dry column gives the desired product.

Fuente