Acetic Acid → Dimethyl 3-(cyanomethylidene)pentanedioate

HRID 552323노트

반응식

HRID 552323 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[C:13]([CH2:15]C(O)=O)#[N:14].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=[CH:15][C:13]#[N:14])[CH2:6][C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 9740Cyanoacetic acidHCID 74591Dimethyl 3-oxoglutarate

생성물 1

HCID 254955Dimethyl 3-(cyanomethylidene)pentanedioate수율 68.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 3-oxo-pentanedioic acid dimethyl ester (523 g) in toluene (750 mL), cyanoacetic acid (511 g), NH4OAc (46.3 g) and acetic acid (90.1 g) were added and heated at reflux with dehydrating by Dean-Stark apparatus for 8 h. After cooling to room temperature, the reaction mixture was washed with water, saturated aqueous NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to give crude 3-cyanomethylene-pentanedioic acid dimethyl ester (403 g) as an oil. 1H NMR (200 MHz, CDCl3) δ ppm 3.39 (d, J=0.88 Hz, 2 H), 3.62 (s, 2 H), 3.72 (s, 3 H), 3.74 (s, 3 H), 5.51 (s, 1 H).

후처리

  1. temperatureheated
  2. temperatureat reflux with dehydrating by Dean-Stark apparatus for 8 h
  3. washthe reaction mixture was washed with water, saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8707aa4769d24718a1ef1f2b54279d00
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951811B2

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