Reacción #415077

Ecuación de reacción

(E,E)-Farnesol

dimethyl diazomethylphosphonate

→

ether

Rendimiento 36.4%

(E,E)-[[(3,7,11-Trimethyl-2,6,10-dodecatrienyl)oxy]methyl]phosphonic acid, dimethyl ester

Rendimiento 36.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroof dry
2. 2
   Otrodeoxygenated benzene (10 ml)
3. 3
   workup.ADDITIONtreated in one portion with ##STR87## (1.0 mmol, 0.442 g)
4. 4
   Otro10, pages 1379 to 1386) in 20 ml of dry
5. 5
   Otrodeoxygenated benzene
6. 6
   workup.ADDITIONwas added dropwise over 4 hours via syringe pump
7. 7
   workup.ADDITIONAfter addition
8. 8
   workup.STIRRINGthe reaction mixture was stirred an additional 45 minutes
9. 9
   Lavadoeluted with 75% ethyl acetate/hexane

Procedimiento

(E,E)-Farnesol, (5.0 mmol, 1.11 g, 1.26 ml) was stirred under argon in 10 ml of dry deoxygenated benzene (10 ml) and treated in one portion with ##STR87## (1.0 mmol, 0.442 g). The dark blue/green solution was stirred at room temperature and a solution of (1.5 g, 10.0 mmol) of dimethyl diazomethylphosphonate (prepared according to D. Seyferth et al, J. Org. Chem., 1971, vol. 36, No. 10, pages 1379 to 1386) in 20 ml of dry, deoxygenated benzene was added dropwise over 4 hours via syringe pump. After addition, the reaction mixture was stirred an additional 45 minutes. The reaction mixture was stripped of solvent and applied as a 75% ethyl acetate/Hexane solution to a flash chromatography column (50 mm diameter, 6" of silica gel) eluted with 75% ethyl acetate/hexane to afford 0.627 g, (36% yield), of the ether as a dark blue/green oil.

Fuente