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

HRID 1860680ノート

反応式

HRID 1860680 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-445044ea221c4ecf8a52f50358bcbc5f
出典データセット
uspto-grants-2003_03
特許番号
US06531494B1

反応ノート

読み込み中…