Hydrochloric Acid → Cholesta-5,7-diene-1,3-diol

HRID 1708830ノート

反応式

HRID 1708830 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].CS(O[CH:12]([C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27]([CH2:28][C@@H:29]([O:46]C4CCCCO4)[CH2:30][C@@H:31]2[O:39]C2CCCCO2)=[CH:26][CH:25]=3)[CH2:22][CH2:21]1)[CH3:19])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])(=O)=O.Cl>O1CCCC1.O>[CH3:17][CH:15]([CH2:14][CH2:13][CH2:12][C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27]([CH2:28][C@@H:29]([OH:46])[CH2:30][C@@H:31]2[OH:39])=[CH:26][CH:25]=3)[CH2:22][CH2:21]1)[CH3:19])[CH3:16]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 867458381alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate

生成物 1

HCID 193829Cholesta-5,7-diene-1,3-diol収率 45.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 0.10 g of lithium aluminum hydride in 5 ml of tetrahydrofuran was added 0.66 g of 1α,3β-bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate under heating and the mixture was refluxed for 2 hours. The resulting reaction mixture was cooled and, then, water and diluted hydrochloric acid were added in succession. The mixture was stirred at room temperature for 2 hours. The resulting solution was diluted with water and extracted with diethyl ether. The extract was washed with diluted hydrochloric acid and aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The low-boiling fraction was then distilled off and the residue was purified by silica gel column chromatography and recrystallized from methanol. The procedure yielded 0.18 g of cholesta-5,7-diene-1α,3β-diol (yield: 45%) showing the following physical properties.

後処理

  1. temperatureunder heating
  2. temperaturethe mixture was refluxed for 2 hours
  3. customThe resulting reaction mixture
  4. temperaturewas cooled
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with diluted hydrochloric acid and aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe low-boiling fraction was then distilled off
  9. customthe residue was purified by silica gel column chromatography
  10. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-195434503447468991ab34b7409e69ba
出典データセット
uspto-grants-1994_10
特許番号
US05359055

反応ノート

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