Reacción #3993

Ecuación de reacción

acetyl chloride

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

pyridine

→

titled compound

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

Disolventes

methylene chloride

methylene chloride

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat room temperature for 30 minutes
2. 2
   LavadoThe solution is washed with ice cold 5% aqueous sodium bicarbonate and water
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated
5. 5
   Otroto give the crude product
6. 6
   Otrorecrystallization from ethanol

Procedimiento

A solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol (1.6 g, 5 mmol) and pyridine (9.6 ml, 7.3 mmol) in 15 ml of anhydrous methylene chloride is stirred in an ice bath and a solution of acetyl chloride (0.37 ml, 5.25 mmol) in 5 ml of anhydrous methylene chloride is added dropwise. The mixture is stirred at 0° C. for 11/2 hours and at room temperature for 30 minutes and then taken up in 250 ml of ether. The solution is washed with ice cold 5% aqueous sodium bicarbonate and water, dried (MgSO4) and evaporated to give the crude product; recrystallization from ethanol affords the titled compound.

Fuente