반응 #2157763

반응 방정식

sodium hydride

potassium tert-butoxide

spiro[5.5]undecan-1-one

dimethyl carbonate

→

1-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

용매

tetrahydrofuran

brine

acetic acid

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도under reflux
3. 3
   온도by heating the reaction mixture
4. 4
   온도under reflux for 2 hours
5. 5
   온도After ice-cooling
6. 6
   추출followed by extraction with ethyl acetate
7. 7
   세척The organic layer was washed with saturated brine
8. 8
   기타dried
9. 9
   농축concentrated
10. 10
    기타The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15)

실험 절차

To a suspension of 60% sodium hydride (5.7 g) and potassium tert-butoxide (1.6 g) in tetrahydrofuran (200 mL) was added dimethyl carbonate (9.6 mL) at room temperature while stirring. The reaction mixture was heated under reflux. To the reaction mixture was added dropwise a solution of spiro[5.5]undecan-1-one (11.85 g) obtained in Step 1 in tetrahydrofuran (40 mL) over 1 hour, followed by heating the reaction mixture under reflux for 2 hours. After ice-cooling, acetic acid (14.6 mL) was added dropwise to the reaction mixture. Then, the reaction mixture was poured into saturated brine, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15) to give 1-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (13.02 g).

출처