Reaction #1702023

Reaction equation

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)

Solvents

toluene

Conditions

Workup

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

Procedure

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).

Source