Acetic Acid → 2-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl Ester

HRID 1860680노트

반응식

HRID 1860680 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:13]#[N:14])=[C:10]([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:20]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 517165Ammonium Acetate

생성물 1

HCID 600747842-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl Ester수율 64.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In a flask equipped with a Dean-stark trap was prepared a solution of 1-(4-Methoxy-phenyl)-propan-2-one (40 g), ethyl cyanoacetate (27.56 g), ammonium acetate (9.40 g), acetic acid (14.64 g) and toluene (150 ml) at room temperature. The solution was heated to reflux overnight. The solution was cooled to room temperature, washed with water and brine, and concentrated. The crude product was purified on a silica gel column, eluting with 10% ethyl acetate/hexane to afford colorless oil (40.76 g). The 1H NMR was consistent with the proposed structure.

후처리

  1. customIn a flask equipped with a Dean-stark trap
  2. temperatureThe solution was heated
  3. temperatureto reflux overnight
  4. washwashed with water and brine
  5. concentrationconcentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with 10% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-445044ea221c4ecf8a52f50358bcbc5f
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531494B1

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