تفاعل #415077

معادلة التفاعل

(E,E)-Farnesol

dimethyl diazomethylphosphonate

→

ether

المردود 36.4%

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

المردود 36.4%

ظروف التفاعل

المعالجة

1. 1
   أخرىof dry
2. 2
   أخرىdeoxygenated benzene (10 ml)
3. 3
   workup.ADDITIONtreated in one portion with ##STR87## (1.0 mmol, 0.442 g)
4. 4
   أخرى10, pages 1379 to 1386) in 20 ml of dry
5. 5
   أخرىdeoxygenated 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
   غسيلeluted with 75% ethyl acetate/hexane

الإجراء التجريبي

(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.

المصدر