Tetrahydrofuran → Estra-1,3,5(10),16-tetraen-3,6-diol

HRID 582853

反応式

HRID 582853 の反応式
[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

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 21226445Aluminium lithium hydride2 回HCID 22873077Estra-1,3,5(10),16-tetraen-6-one-3-yl-acetate

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28a30ec14a2f4c2896559f1f8711a436
出典データセット
uspto-grants-1999_07
特許番号
US05925774

関連ノート

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