تفاعل #64425

معادلة التفاعل

methanol

N-heptyl-N-ethyladipamic acid, methyl ester

sodium borohydride

→

N-heptyl-N-ethyl(6-hydroxy)hexanamide

المردود 35.8%

المذيبات

tert-butanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis heated
2. 2
   درجة الحرارةto reflux
3. 3
   workup.ADDITIONis added dropwise
4. 4
   درجة الحرارةat reflux for 18 hours
5. 5
   أخرىpartitioned between water and CH2Cl2
6. 6
   أخرىAfter separation
7. 7
   تجفيفthe organic layer is dried over MgSO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated under vacuum
10. 10
    أخرىThe residue obtained
11. 11
    أخرىchromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate

الإجراء التجريبي

A mixture of a solution of 3.1 gms of the N-heptyl-N-ethyladipamic acid, methyl ester in 40 ml of tert-butanol and 800 mg of sodium borohydride is heated to reflux, following which 7.8 ml of methanol is added dropwise. The reaction mixture is stirred at reflux for 18 hours and then partitioned between water and CH2Cl2. After separation, the organic layer is dried over MgSO4, filtered, and concentrated under vacuum. The residue obtained is flash chromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate to yield 1.0 gms of N-heptyl-N-ethyl(6-hydroxy)hexanamide.

المصدر