Reacción #1553914

Ecuación de reacción

(E,E)-farnesyl bromide

NH4OH

3-methoxy-5-bromotoluene

n-BuLi

NH4Cl

→

compound 24

Rendimiento 80.9%

1-methoxy-3-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzene

Rendimiento 80.9%

Disolventes

THF

Et2O

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for another 10 min at the same temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 2 hours at −78° C
4. 4
   LavadoThe combined organic layer was washed with water, brine
5. 5
   Secadodried with Na2SO4
6. 6
   OtroThe crude product was purified by flash silica gel chromatography (hexanes/EtOAc 60:1, 30:1, 20:1 and 10:1)

Procedimiento

To a solution of 3-methoxy-5-bromotoluene (0.50 g, 2.49 mmol) in dry THF (8 mL) was added n-BuLi (1.71 mL, 2.74 mmol, 1.6 M in Hexane) dropwise at −78° C. After the reaction mixture was stirred for 15 min, Li2CuCl4 (0.1 mL, 0.1 mmol, 0.1 M in THF) was added, and the mixture was stirred for another 10 min at the same temperature. Then, a solution of (E,E)-farnesyl bromide (0.70 mL, 2.58 mmol) in THF (3 ml) was added over 0.5 hour and stirring was continued for 2 hours at −78° C. After the reaction was complete, the mixture was warmed to room temperature and saturated aqueous NH4Cl (20 mL) was added, followed by 10% NH4OH (40 mL) and Et2O (3×50 mL). The combined organic layer was washed with water, brine, and dried with Na2SO4. The crude product was purified by flash silica gel chromatography (hexanes/EtOAc 60:1, 30:1, 20:1 and 10:1) to yield compound 24 (658.1 mg, 78%) as a colorless oil.

Fuente