Sulfuric Acid → HCID 15871124, compound

HRID 2187287Notes

Reaction equation

HRID 2187287 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH:15]=[C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:28])[CH2:17]4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C1(=O)CCCCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=[O:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 11143Aluminum isopropoxideHCID 1298468-Dehydrocholesterol

Product 1

HCID 15871124HCID 15871124, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7967CyclohexanoneSolvent

Procedure

A solution of 2.20 g cholesta-5,8-dien-3β-ol in 27 ml toluene and 6 ml cyclohexanone is refluxed for 10 minutes in a Dean-Stark apparatus. 0.57 g aluminum isopropoxide are added and the reaction mixture is refluxed for 30 minutes. After cooling and addition of sulfuric acid (2 N), the resulting mixture is extracted with ethyl acetate. The organic layer is separated, washed with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of hexane and ethyl acetate to give 1.53 g cholesta-4,8-dien-3-one as a white solid.

Workup

  1. temperaturethe reaction mixture is refluxed for 30 minutes
  2. temperatureAfter cooling
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with saturated sodium bicarbonate solution and water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customAfter evaporation of the solvent the residue
  9. customis chromatographed with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-d60d95de93c94bd0a509a4c790034f67
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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