聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 7alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-triene-3,17alpha-diol

HRID 361663笔记

反应方程式

HRID 361663 反应方程式
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[C@H:11]([F:27])[CH2:10]1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].O.S(=O)(=O)(O)O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C@H:12]([OH:26])[C@H:11]([F:27])[CH2:10]1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 1118四氧化硫HCID 16710494三叔丁氧基氢化铝锂HCID 229418077alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-trien-3-ol-17-one

产物 1

HCID 155422577alpha-(5-Chloropentyl)-16alpha-fluoro-estra-1,3,5(10)-triene-3,17alpha-diol收率 35%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
0 °C

实验过程

392 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-trien-3-ol-17-one, Example 15d), in 2 ml of anhydrous tetrahydrofuran is dissolved, and 1.1 ml of a 1-molar solution of lithium tri-tert-butoxyaluminum hydride in tetrahydrofuran is added while being cooled in an ice bath. It is allowed to stir for 30 minutes at 0° C., then mixed with water and 8% sulfuric acid until a weakly acidic reaction is achieved, and it is extracted three times with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried with sodium sulfate and evaporated to dryness in a vacuum. The crude product is chromatographed on silica gel with hexane/ethyl acetate, whereby 118 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17β-diol and 138 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17α-diol is obtained, both as a solid foam.

后处理

  1. temperaturewhile being cooled in an ice bath
  2. extractionit is extracted three times with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness in a vacuum
  6. customThe crude product is chromatographed on silica gel with hexane/ethyl acetate, whereby 118 mg of 7α-(5-chloropentyl)-16α-fluoro-estra-1,3,5(10)-triene-3,17β-diol

来源与证据

ORD记录
ord-0b758f18e4144d089bc004fe05133a93
来源数据集
uspto-grants-1999_02
专利号
US05866560

反应笔记

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