2,2’-[(1-甲基亚乙基)二(4,1-亚苯基氧亚甲基)]二环氧乙烷与α-氢-ω-羟基聚(氧-1,2-亚乙基)的聚合物 → 3-Hydroxy-5beta-estran-17-one ethylene ketal

HRID 7412

反应方程式

HRID 7412 反应方程式
[OH:1][CH:2]1[CH2:19][CH2:18][C@H:17]2[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:20])[CH2:3]1.[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOC(C)=O.CCCCCC>C1C=CC=CC=1.CCOC(C)=O>[CH2:22]1[O:23][C:11]2([CH2:10][CH2:9][C@H:8]3[C@H:7]4[C@H:16]([CH2:15][CH2:14][C@:12]23[CH3:13])[C@@H:17]2[C@@H:4]([CH2:3][CH:2]([OH:1])[CH2:19][CH2:18]2)[CH2:5][CH2:6]4)[O:20][CH2:21]1

参与物

7

反应物 4

HCID 1742,2’-[(1-甲基亚乙基)二(4,1-亚苯基氧亚甲基)]二环氧乙烷与α-氢-ω-羟基聚(氧-1,2-亚乙基)的聚合物HCID 4661024-甲基苯磺酸吡啶HCID 21226206Ethyl acetate hexaneHCID 227956593-Hydroxy-5betaestran-17-one

产物 1

HCID 867601793-Hydroxy-5beta-estran-17-one ethylene ketal收率 94.8%

试剂、催化剂与溶剂 2

HCID 241苯溶剂HCID 8857乙酸乙酯溶剂

实验过程

Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.

后处理

  1. temperaturerefluxed
  2. washwashed twice with brine
  3. customdried on Na2SO4
  4. customthe solvents removed under reduced pressure

来源与证据

ORD记录
ord-faa2f348d6f5478eb5c5bd468fd5e72f
来源数据集
uspto-grants-2006_08
专利号
US07087590B2

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