Hydrogen Peroxide → HCID 69770587、化合物

HRID 861808ノート

反応式

HRID 861808 の反応式
[C:1]([O:9][CH:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH:17]=4)[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[OH-:40].[Na+].OO>C1COCC1.C(OCC)C.O>[C:1]([O:9][CH:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[CH:12]([CH2:13][CH2:14][C:15]3[C@H:16]4[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH:17]4[OH:40])[C:11]1([CH3:38])[CH3:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 54120485HCID 54120485、化合物

生成物 1

HCID 69770587HCID 69770587、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2.04 g of 3-benzoyloxy-4,4-dimethylcholesta-8,14-diene (Step A) was dissolved in 50 ml of THF, and 360 ml of 1M borane in THF was added dropwise at 0° C. The mixture was stirred at ambient temperature overnight, cooled to 0° C., and 140 ml of water was added dropwise, followed by 360 ml of 10% sodium hydroxide and 378 ml of 30% hydrogen peroxide. After stirring for 90 mutes, 100 ml of diethyl ether was added to the mixture and the aqueous phase extracted twice with diethyl ether. The combined organic phases were washed twice with sodium bisulphite solution and then with water. After evaporation, the product was purified by chromatography on SiO2 (2% diethyl ether in toluene) to yield 0.62 g of 3-benzoyloxy-4,4-dimethylcholest-8-en-15-ol.

後処理

  1. temperaturecooled to 0° C.
  2. additionwas added to the mixture
  3. extractionthe aqueous phase extracted twice with diethyl ether
  4. washThe combined organic phases were washed twice with sodium bisulphite solution
  5. customAfter evaporation
  6. customthe product was purified by chromatography on SiO2 (2% diethyl ether in toluene)

出典と根拠

ORDレコード
ord-4bef146b0f5c473994072438a75473b7
出典データセット
uspto-grants-1998_02
特許番号
US05716777

反応ノート

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