1,2-环己二酮 → 4-氧杂-4,5,6,7-四氢苯并[B]呋喃-3-羧酸

HRID 899

反应方程式

HRID 899 反应方程式
[OH-:1].[K+].[C:3]1(=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.Br[CH2:12][C:13](=O)[C:14]([O:16]CC)=[O:15].[OH-].[Na+]>CO.O>[O:10]=[C:3]1[C:4]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][O:1][C:5]=2[CH2:6][CH2:7][CH2:8]1

参与物

7

反应物 4

HCID 130061,2-环己二酮HCID 14797氢氧化钾HCID 14798二甲基对苯二胺二盐酸HCID 661443-溴丙酮酸乙酯

产物 1

HCID 7139374-氧杂-4,5,6,7-四氢苯并[B]呋喃-3-羧酸

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂3 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
0 °C

实验过程

4-Oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid was prepared as follows: To a stirred solution of potassium hydroxide (28.06 g, 0.5 mol) in methyl alcohol (100 mL) under nitrogen at 0° C. was added dropwise a solution of cyclohexanedione (56.07 g, 0.5 mol) in methyl alcohol (100 mL). The mixture was stirred at 0° C. for 0.5 h, then a solution of ethyl bromopyruvate (66 mL, 0.525 mol) in methyl alcohol(100 mL) was added dropwise. After allowing the mixture to stir at ambient temperature for 17 h, a 50% aqueous sodium hydroxide solution (60 mL) was added dropwise and stirring continued an additional 7 h. After dilution with water, the solution was acidified and the methanol removed in vacuo. Ice water was added and the precipitate filtered and dried in vacuo to afford 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid. m.p. 137°-138° C.

后处理

  1. custom4-Oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid was prepared
  2. stirringto stir at ambient temperature for 17 h
  3. stirringstirring
  4. waitcontinued an additional 7 h
  5. customthe methanol removed in vacuo
  6. additionIce water was added
  7. filtrationthe precipitate filtered
  8. customdried in vacuo

来源与证据

ORD记录
ord-754d50c008364ac9b11186dee1fd24b1
来源数据集
uspto-grants-1998_03
专利号
US05723462

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