反応 #1702023

反応方程式

Compound ( 1-B )

(E)-4-(2,2-difluorovinyl)-4′-(prop-1-en-1-yl)-1,1′-bi(cyclohexane)

sodium bis(2-methoxyethoxy)aluminum dihydride toluene

hydrochloric acid

→

compound ( 1-1 )

4-((E)-2-fluorovinyl)-4′-((E)-prop-1-en-1-yl)-1,1′-bi(cyclohexane)

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   抽出extraction
3. 3
   洗浄An organic layer was washed with a saturated aqueous solution of sodium chloride
4. 4
   乾燥a saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他thus a colorless oily matter was obtained
7. 7
   その他The resultant material was subjected to silica gel column chromatography (heptane) and recrystallization at a low temperature

実験手順

Compound (1-B) (5.0 g) obtained in the above operation was dissolved in toluene (50 ml), and a 65% sodium bis(2-methoxyethoxy)aluminum dihydride toluene solution (8.0 ml) was added dropwise. After completion of the reaction, 1N hydrochloric acid was added, and extraction was carried out with toluene. An organic layer was washed with a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a colorless oily matter was obtained. The resultant material was subjected to silica gel column chromatography (heptane) and recrystallization at a low temperature by using Solmix A-11 (registered trademark) (Japan Alcohol Trading Co., Ltd.), and thus compound (1-1) was obtained as a colorless oily matter (1.2 g).

出典