반응 #5805

반응 방정식

diethyl ether

t-butyl alcohol

(±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]-undecane-2-acetic acid

dicyclohexylcarbodiimide

→

(±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도to slowly warm to room temperature over a 16.5-hour period
2. 2
   workup.STIRRINGThe mixture is stirred one hour
3. 3
   workup.STIRRINGstirring continued four hours
4. 4
   여과filtered
5. 5
   농축The filtrate is concentrated at reduced pressure
6. 6
   농축This crude concentrate
7. 7
   기타is chromatographed on silica gel
8. 8
   세척eluted with 4:1 hexane

실험 절차

(±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]-undecane-2-acetic acid 3.32 g (13.12 mmol), is dissolved in 15 mL of dichloromethane, cooled to 0° C. and 0.1 g of 4-dimethylaminopyridine (DMAP) added, followed y t-butyl alcohol, and followed by 3.25 g of dicyclohexylcarbodiimide (DCC). This solution is stirred and allowed to slowly warm to room temperature over a 16.5-hour period. TLC shows mainly product, and some slightly lower Rf by-product. The mixture is stirred one hour and 50 mL of dichloromethane is added and stirring continued four hours. One hundred mL of diethyl ether is added and then filtered. The filtrate is concentrated at reduced pressure. This crude concentrate is chromatographed on silica gel and eluted with 4:1 hexane:ethyl acetate to yield (±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate.

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