Réaction #3994

Équation de réaction

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

Solvants

THF

HMPA

diethyl ether

Conditions de réaction

Traitement

1. 1
   LavageThe solution is washed with saturated aqueous NH4Cl and water
2. 2
   Autredried
3. 3
   Autreannd evaporated in vacuo
4. 4
   Autreto give an oil
5. 5
   AutrePurification on a silica gel
6. 6
   Autredry column

Mode opératoire

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.

Source