반응 #310114

반응 방정식

4-(benzyloxy)benzaldehyde

sodium cyanoborohydride

p-toluenesulfonic acid monohydrate

pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate

3-hydrazinopropanenitrile

4-(benzyloxy)benzaldehyde

sodium cyanoborohydride

p-toluenesulfonic acid monohydrate

→

title compound

수율 61.3%

3-chloro-N′-(2-cyanoethyl)-4-[(1-methylethyl)oxy]-N′-({4-[(phenylmethyl)oxy]phenyl}methyl)benzohydrazide

수율 61.3%

용매

methanol

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 1 h
3. 3
   온도Following cooling
4. 4
   workup.STIRRINGthe solution stirred overnight at ambient temperature
5. 5
   기타The reaction was quenched with 6N aqueous NaOH
6. 6
   workup.ADDITIONdiluted with brine
7. 7
   추출extracted thrice with EtOAc
8. 8
   건조The organic layer was dried over MgSO4
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타Purification via flash column chromatography (30-80% EtOAc/hexanes)

실험 절차

A solution of pentafluorophenyl 3-chloro-4-[(1-methylethyl)oxy]benzoate (0.100 g, 0.263 mmol) in methanol (5.0 mL) was treated with 3-hydrazinopropanenitrile (0.023 mL, 0.289 mmol) and heated to reflux for 1 h. Following cooling, 4-(benzyloxy)benzaldehyde (0.067 g, 0.315 mmol), sodium cyanoborohydride (0.020 g, 0.315 mmol), and p-toluenesulfonic acid monohydrate (0.060 g, 0.315 mmol) were added and the solution stirred 30 min. at ambient temperature. Additional 4-(benzyloxy)benzaldehyde (0.067 g, 0.315 mmol), sodium cyanoborohydride (0.040 g, 0.637 mmol), and p-toluenesulfonic acid monohydrate (0.100 g, 0.526 mmol) were added and the solution stirred overnight at ambient temperature. The reaction was quenched with 6N aqueous NaOH, diluted with brine, and extracted thrice with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification via flash column chromatography (30-80% EtOAc/hexanes) gave the title compound as a white solid (0.077 g; 61%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.61 (d, J=2.3 Hz, 1H) 7.45 (dd, J=8.8, 2.2 Hz, 2H) 7.42 (s, 1H) 7.36-7.41 (m, 2H) 7.32 (tt, J=7.0, 1.8 Hz, 1H) 7.28 (s, 1H) 7.17 (br. s., 1H) 6.94 (d, J=8.6 Hz, 2H) 6.88 (d, J=8.6 Hz, 1H) 5.05 (s, 2H) 4.61 (qq, J=6.0 Hz, 1H) 4.22 (s, 2H) 3.39 (t, J=6.6 Hz, 2H) 2.60 (t, J=6.6 Hz, 2H) 1.39 (d, J=6.1 Hz, 6H). MS (ES+) m/e 478 [M+H]+.

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