Ethanol → Cholesta-1,5,7-triene-3beta,25-diol

HRID 2397525ノート

反応式

HRID 2397525 の反応式
C(O)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[CH3:9][C:10]([OH:37])([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C:26](=[O:36])[CH:27]=[CH:28]2)=[CH:23][CH:22]=3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11]>C(O)(=O)C.CCOCC.CO>[CH3:9][C:10]([OH:37])([CH2:12][CH2:13][CH2:14][C@H:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C@@H:26]([OH:36])[CH:27]=[CH:28]2)=[CH:23][CH:22]=3)[CH2:19][CH2:18]1)[CH3:16])[CH3:11]

参加物

8

反応物 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 22797385Cholesta-1,5,7-trien-3-on-25-ol

生成物 1

HCID 22817251Cholesta-1,5,7-triene-3beta,25-diol

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
10 °C

実験手順

100 ml of an ethanol solution containing 2.5 g of sodium borohydride was added dropwise under agitation to 110 ml of methanol containing 4.9 g of calcium chloride, which was cooled below - 10° C. The mixture was agitated for 20 minutes while maintaining the temperature at about -10° C. Then, 100 ml of the ether solution containing crude cholesta-1,5,7-trien-3-on-25-ol, which was prepared in (1.) above, was added dropwise to the above mixture. The reaction mixture was further agitated at -10° C. for 1 hour and at 0° C. for 1 hour, and was then neutralized with 10% acetic acid after which the solvent was distilled off under reduced pressure. The residue was extracted with methylene chloride and the extract was washed with water and dried with magnesium sulfate. Methylene chloride was distilled off to obtain crude cholesta-1,5,7-triene-3β,25-diol (about 1 g).

後処理

  1. temperaturewhile maintaining the temperature at about -10° C
  2. customwas prepared in (1.) above,
  3. additionwas added dropwise to the above mixture
  4. stirringThe reaction mixture was further agitated at -10° C. for 1 hour and at 0° C. for 1 hour
  5. distillationwas distilled off under reduced pressure
  6. extractionThe residue was extracted with methylene chloride
  7. washthe extract was washed with water
  8. dry with materialdried with magnesium sulfate
  9. distillationMethylene chloride was distilled off

出典と根拠

ORDレコード
ord-d97d4e23a93a40ddbbab352b21af1f87
出典データセット
uspto-grants-1977_05
特許番号
US04022768

反応ノート

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