四氢呋喃 → Estra-1,3,5(10),16-tetraen-3,6-diol

HRID 369696笔记

反应方程式

HRID 369696 反应方程式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@:8]12[CH2:24][CH2:23][C@H:22]3[C@@H:13]([CH2:14][C:15](=[O:29])[C:16]4[CH:17]=[C:18](CC([O-])=O)[CH:19]=[CH:20][C:21]=43)[C@@H:12]1[CH2:11][CH:10]=[CH:9]2.C1C[O:33]CC1>>[CH3:7][C@:8]12[CH2:24][CH2:23][C@H:22]3[C@@H:13]([CH2:14][CH:15]([OH:29])[C:16]4[CH:17]=[C:18]([OH:33])[CH:19]=[CH:20][C:21]=43)[C@@H:12]1[CH2:11][CH:10]=[CH:9]2

参与物

4

反应物 3

HCID 8028四氢呋喃2 次HCID 21226445Aluminium lithium hydride2 次HCID 22873077Estra-1,3,5(10),16-tetraen-6-one-3-yl-acetate

产物 1

HCID 15870995Estra-1,3,5(10),16-tetraen-3,6-diol收率 10%

实验过程

To a suspension of lithium aluminum hydride (LAH, 95%, 46.9 mg, 1.17 mmol) in 5 mL of anhydrous THF was added estra-1,3,5(10),16-tetraen-6-one-3-yl-acetate (6) (422.9 mg, 1.360 mmol) in 5 mL of anhydrous THF dropwise, with stirring. The reaction was stirred 50 min., after which further LAH (46.5 mg, 1.16 mmol) was added and the reaction stirred 22 h. After refluxing 4 h TLC still showed starting material. The reaction was quenched with 0.5 mL of water+0.5 mL of 20% (w/w) sulfuric acid and concentrated under reduced pressure. The residue was extracted four times with 10 mL portions of hot ethyl acetate and filtered through Celite. The combined filtrates were concentrated and purified twice by flash chromatography to give solid product (0.05 g, 0.2 mmol, 10%), m.p. 150-157° C.

后处理

  1. stirringThe reaction was stirred 50 min.
  2. stirringthe reaction stirred 22 h
  3. temperatureAfter refluxing 4 h TLC
  4. customThe reaction was quenched with 0.5 mL of water+0.5 mL of 20% (w/w) sulfuric acid
  5. concentrationconcentrated under reduced pressure
  6. extractionThe residue was extracted four times with 10 mL portions of hot ethyl acetate
  7. filtrationfiltered through Celite
  8. concentrationThe combined filtrates were concentrated
  9. custompurified twice by flash chromatography

来源与证据

ORD记录
ord-299a6fe9d7414c8e97b7b4bf472d5c09
来源数据集
uspto-grants-2000_10
专利号
US06140316

反应笔记

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