반응 #217749

반응 방정식

2-cyano-3-isopropyl-hexanoic acid methyl ester

NaH

t-butyl bromoacetate

→

2-Cyano-2-(1-isopropyl-butyl)-succinic acid 4-tert-butyl ester 1-methyl ester

용매

THF

THF

반응 조건

후처리

1. 1
   온도is cooled in an ice water bath under argon
2. 2
   workup.WAITAfter 12 hours
3. 3
   기타the reaction is quenched by addition of 50 mL of saturated KH2PO4
4. 4
   기타the THF is evaporated
5. 5
   추출The organic products are extracted into Et2O (3×50 mL)
6. 6
   건조the combined organic layers are dried over MgSO4
7. 7
   기타The solvent is evaporated

실험 절차

A solution of 2-cyano-3-isopropyl-hexanoic acid methyl ester (1.9 g, 9.6 mmol) in 10 mL of THF is added to a slurry of NaH (washed with hexane, 0.23 g, 9.6 mmol) in 20 mL of THF which is cooled in an ice water bath under argon. The solution is stirred for 10 minutes, and t-butyl bromoacetate (2.1 g, 10.6 mmol) is added. The solution is warmed to room temperature. After 12 hours, the reaction is quenched by addition of 50 mL of saturated KH2PO4 and the THF is evaporated. The organic products are extracted into Et2O (3×50 mL), and the combined organic layers are dried over MgSO4. The solvent is evaporated, and the remaining oil is chromographed under medium pressure over silica gel in 25% hexane/CH2Cl2. Yield of 2-cyano-2-(1-isopropyl-butyl)-succinic acid 4-tert-butyl ester 1-methyl ester=1.3 g (42%) as an oil.

출처