반응 #5757

반응 방정식

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

수율 70.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   추출the reaction mixture was extracted with ether
2. 2
   건조The extract was dried over Na2SO4
3. 3
   기타evaporated in vacuo
4. 4
   기타to remove the solvent
5. 5
   기타to give a crude product, which
6. 6
   기타was purified with silica gel column chromatography

실험 절차

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.

출처