반응 #215968

반응 방정식

sodium bicarbonate

sodium hydroxide

triethyl 2-phosphonopropionate

sodium hydride

diisobutylaluminum hydride

5-(2,6,6-trimethyl-1-cyclohexen-1-yl)pentanal

→

(2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenol

수율 43.1%

용매

THF

toluene

반응 조건

후처리

1. 1
   온도at reflux for16 hr
2. 2
   온도The reaction is cooled
3. 3
   추출extracted with ether
4. 4
   농축The extracts are concentrated
5. 5
   기타chromatographed with 30% dichloromethane in hexane
6. 6
   기타to provide (2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenoic
7. 7
   workup.STIRRINGstirred at 0° for 3 hr
8. 8
   추출The mixture is extracted with ether
9. 9
   농축the organic phase is concentrated
10. 10
    기타chromatographed with dichloromethane

실험 절차

To a stirred solution of triethyl 2-phosphonopropionate (4.2 g) in THF (25 ml) under nitrogen is added sodium hydride (0.69 g of 60% dispersion in oil). After 30 minutes, 5-(2,6,6-trimethyl-1-cyclohexen-1-yl)pentanal (3.09 g) is added, and the mixture is stirred at reflux for16 hr. The reaction is cooled, poured into aqueous sodium bicarbonate, and extracted with ether. The extracts are concentrated and chromatographed with 30% dichloromethane in hexane to provide (2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenoic add ethyl ester as a colorless oil (2.4 g). This material (2.09 g) is reacted with diisobutylaluminum hydride (10 ml of 1.5M toluene solution) in toluene (20 ml) at -20° , stirred at 0° for 3 hr, then stirred for 16 hr with 1.0N sodium hydroxide solution. The mixture is extracted with ether, and the organic phase is concentrated and chromatographed with dichloromethane to provide 1.6 g of (2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenol as a colorless oil.

출처