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

HRID 1196399Notes

Reaction equation

HRID 1196399 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bceb443ccc514b358e4e50f418154551
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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