تفاعل #5757

معادلة التفاعل

6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one

vinylmagnesium bromide

ammonium chloride

→

3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol

المردود 70.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe reaction mixture was extracted with ether
2. 2
   تجفيفThe extract was dried over Na2SO4
3. 3
   أخرىevaporated in vacuo
4. 4
   أخرىto remove the solvent
5. 5
   أخرىto give a crude product, which
6. 6
   أخرىwas purified with silica gel column chromatography

الإجراء التجريبي

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred for 10 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol (61 mg, 70%). IR(film)cm-1 ; 3460, 2950, 2880, 1200, 1118, 1075, 1022, 905, 865, 810.

المصدر