Reaktion #1702023

Reaktionsgleichung

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)

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionextraction
3. 3
   WaschenAn organic layer was washed with a saturated aqueous solution of sodium chloride
4. 4
   Trocknena saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   Sonstigethus a colorless oily matter was obtained
7. 7
   SonstigeThe resultant material was subjected to silica gel column chromatography (heptane) and recrystallization at a low temperature

Vorschrift

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).

Quelle