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

HRID 1682539노트

반응식

HRID 1682539 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 6228Dimethylformamide용매

실험 절차

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%). 1H-NMR (CDCl3):8.60 (s, 1H); 7.66 (s, 1H); 7.60-7.02 (m, 9H); 3.92 (s, 3H); 2.42 (s, 3H).

후처리

  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

출처 및 근거

ORD 기록
ord-23c0dd808f55456e975bfac4096e1057
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635508

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