Water → 24-Ketocholesterol

HRID 1154787ノート

反応式

HRID 1154787 の反応式
C([O:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=O)C.[OH-].[K+].O>CO.C1C=CC=CC=1>[OH:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH2:6]1

参加物

6

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 1097227324-Oxocholesterol acetate

生成物 1

HCID 1103680824-Ketocholesterol収率 90%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 887Methanol溶媒2 回

実験手順

Specifically, the crude 3β-acetoxy-24-oxocholest-5-ene was dissolved in 100 ml of a mixture of methanol and benzene (1:1). To the solution was added dropwise a 10% methanol solution of potassium hydroxide at room temperature with stirring. After the addition, the mixture was stirred at 70° C. for 4 hours. After the reaction, 100 mg of water was added to separate the reaction mixture into layers. The resulting aqueous layer was extracted twice with benzene. The benzene extracts were combined with the organic layer. The mixture was washed successively with dilute hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to form 3.6 g (yield: 90% based on 3β-acetoxychol-5-enic acid) of 3β-hydroxy-24-oxocholest-5-ene as a white solid. The properties of the product were as follows:

後処理

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 70° C. for 4 hours
  3. additionwas added
  4. customto separate the reaction mixture into layers
  5. extractionThe resulting aqueous layer was extracted twice with benzene
  6. washThe mixture was washed successively with dilute hydrochloric acid
  7. dry with materiala saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-8f5633944c1c427b80b50a97033e8f6c
出典データセット
uspto-grants-1981_11
特許番号
US04298537

反応ノート

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