丙烯酸乙酯 → Ethyl (3-hydroxy-6-methylpyridin-2-yl)propenoate

HRID 264787

反应方程式

HRID 264787 反应方程式
[OH:1][C:2]1[C:3](I)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36]>CN(C=O)C.O.[Pd](Cl)Cl>[OH:1][C:2]1[C:3]([C:35](=[CH2:36])[C:34]([O:38][CH2:39][CH3:40])=[O:37])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

参与物

8

反应物 4

HCID 8821丙烯酸乙酯HCID 11776三苯基膦HCID 899573-羟基-2-碘-6-甲基吡啶HCID 517044乙酸钾

产物 1

HCID 131720091Ethyl (3-hydroxy-6-methylpyridin-2-yl)propenoate

试剂、催化剂与溶剂 3

HCID 24290氯化钯催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
120 °C

实验过程

To a solution of 3-hydroxy-2-iodo-6-methylpyridine (1.175 g, 5.0 mmol) in DMF (9.5 ml) and water (0.5 ml) were added potassium acetate (1.23 g, 12.5 mmol), triphenylphosphine (105 mg, 0.40 mmol), palladium chloride (36 mg, 0.20 mmol) and ethyl acrylate (1.63 ml, 1.50 g, 15.0 mmol). The mixture was placed under nitrogen and heated at 120° C. for 1.5 h. The mixture was cooled, filtered from deposited palladium black, and added to water (100 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (2×25 ml) and with brine (25 ml), then dried over sodium sulphate and evaporated. This left a tan solid, the product (951 mg, 91%). mp 192°-195° C. (dec)

后处理

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. additionadded to water (100 ml)
  4. extractionThe product was extracted into ethyl acetate (3×30 ml)
  5. washThe combined extracts were washed with water (2×25 ml) and with brine (25 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. waitThis left a tan solid

来源与证据

ORD记录
ord-50a5a9278ade4cedb4d1758badb8b7db
来源数据集
uspto-grants-1997_07
专利号
US05646286

关联笔记

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