p-Toluenesulfonic acid → Methyl alpha-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-beta-methoxyacrylate

HRID 2400129ノート

反応式

HRID 2400129 の反応式
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[C:3]=1[C:21](=[CH:26]N(C)C)[C:22]([O:24][CH3:25])=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:41](=O)(O)[O-:42].[K+].C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(OCC)C.O.CN(C)C=O>[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)[C:3]=1[C:21](=[CH:26][O:42][CH3:41])[C:22]([O:24][CH3:25])=[O:23]

参加物

9

反応物 5

HCID 6101p-Toluenesulfonic acidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 53660927Methyl alpha-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-beta-dimethylaminoacrylate

生成物 1

HCID 54403586Methyl alpha-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-beta-methoxyacrylate収率 85%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

Methyl α-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-β-dimethylaminoacrylate (60 g, 0.15 mol) is dissolved in diethylether (300 ml) and a solution of p-toluene sulfonic acid (44 g, 0.23 mol) in water (200 ml) is added at room temperature with stirring. After 16 hours the mixture is partially neutralized by adding solid potassium bicarbonate (28 g). Extraction of the product with diethylether, drying of the organic phase (MgSO4) and evaporation of the solvent gives the crude enol (52 g, 93%). The product is dissolved in dimethylformamide (100 ml) and potassium carbonate (33 g, 0.24 mol) and dimethyl sulfate (18.9 g, 0.15 mol) is added with cooling. After stirring the reaction mixture at room temperature for 3 hours, diethylether is added and the mixture is washed repeatedly with bring. Drying and chromatography on silicagel (eluant: hexane/ethyl acetate 1:1) gives the pure methyl α-[6-methyl-4(3-phenylphenoxy)-5-pyrimidinyl]-β-methoxyacrylate as a yellowish oil (46 g, 85%).

後処理

  1. extractionExtraction of the product with diethylether
  2. dry with materialdrying of the organic phase (MgSO4) and evaporation of the solvent
  3. customgives the crude enol (52 g, 93%)
  4. temperaturewith cooling
  5. stirringAfter stirring the reaction mixture at room temperature for 3 hours
  6. washthe mixture is washed repeatedly
  7. customDrying

出典と根拠

ORDレコード
ord-06414f43006e402eb13cd4a4a9b3d498
出典データセット
uspto-grants-1995_09
特許番号
US05453427

反応ノート

読み込み中…