Реакция #3994

Уравнение реакции

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

Растворители

THF

HMPA

diethyl ether

Условия реакции

Обработка

1. 1
   ПромывкаThe solution is washed with saturated aqueous NH4Cl and water
2. 2
   Другоеdried
3. 3
   Другоеannd evaporated in vacuo
4. 4
   Другоеto give an oil
5. 5
   ДругоеPurification on a silica gel
6. 6
   Другоеdry column

Методика

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.

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