반응 #527388

반응 방정식

sodium hydrogen carbonate

(2S,3R)-2-octyl-1,3-butanediol

4'-cyano-4-biphenylcarboxaldehyde

sulfuric acid

→

4'-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-cyanobi-phenyl

수율 85.7%

용매

methylene chloride

toluene

ethyl acetate

hexane

water

반응 조건

후처리

1. 1
   기타was placed under nitrogen in a round flask
2. 2
   온도The mixture was heated
3. 3
   온도to reflux for 3 hours
4. 4
   기타while separating water
5. 5
   기타The cooled reaction mixture
6. 6
   기타The aqueous phase was separated
7. 7
   추출extracted twice with methylene chloride
8. 8
   세척The combined organic phases were washed twice with water
9. 9
   건조dried over magnesium sulfate
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타Recrystallization of the crude product
13. 13
    기타obtained (5.84 g)

실험 절차

A mixture of 3.0 g of (2S,3R)-2-octyl-1,3-butanediol, 3.07 g of 4'-cyano-4-biphenylcarboxaldehyde, 0.1 ml of 1N sulfuric acid and 30 ml of toluene was placed under nitrogen in a round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with methylene chloride. The aqueous phase was separated and extracted twice with methylene chloride. The combined organic phases were washed twice with water, dried over magnesium sulfate, filtered and evaporated. Recrystallization of the crude product obtained (5.84 g) from a mixture of 200 ml of hexane and 25 ml of ethyl acetate gave 4.97 g of 4'-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-cyanobi-phenyl with m.p. (C-SA) 114.5° C., cl.p. (SA -I) 128.4° C.

출처