Cholesterol → HCID 53755109, compound

HRID 1855956Notes

Reaction equation

HRID 1855956 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:29]([O-])(O)=O.[Na+].BrN1[C:41](C)(C)[C:39](=[O:40])N(Br)C1=O.N1CC(=O)NC1=O>C(Cl)(Cl)(Cl)Cl>[C:39]([O:19][C@H:18]1[CH2:20][CH2:21][C@@:22]2([CH3:23])[C:16](=[CH:15][CH:14]=[C:13]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:2]([CH3:29])([CH3:1])[CH3:3])[CH2:17]1)(=[O:40])[CH3:41]

Participants

6

Reactant 4

HCID 5997CholesterolHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 10006HydantoinHCID 516892Sodium Bicarbonate

Product 1

HCID 53755109HCID 53755109, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Cholesterol derivative 12 (1 mmole) in 40 ml of CCl4 is treated with 600 mg NaHCO3 and 170 mg of 1,3-dibromo-5,5-dimethyl hydantoin, and the mixture is refluxed under N2 for 3 hours. After cooling to 0° C. the solid hydantoin is removed by filtration. The filtrate is evaporated, the residue is redissolved in 5 ml xylene at 140° C. After 1.5 hours under N2 at this temperature the mixture is cooled to room temperature, diluted with benzene, and washed with 5% HCl, 4% NaHCO3 and saturated NaCl solution. After drying (using Na2SO4) the solvent is evaporated and the residue is chromatographed on AgNO3 -impregnated thin layer plates developed with ethyl acetate/Skellysolve B (1:4). This yields pure 5,7-diene (13) of molecular weight 440 and exhibiting the typical 5,7-diene ultraviolet spectrum.

Workup

  1. temperaturethe mixture is refluxed under N2 for 3 hours
  2. customis removed by filtration
  3. customThe filtrate is evaporated
  4. dissolutionthe residue is redissolved in 5 ml xylene at 140° C
  5. additiondiluted with benzene
  6. washwashed with 5% HCl, 4% NaHCO3 and saturated NaCl solution
  7. dry with materialAfter drying (using Na2SO4) the solvent
  8. customis evaporated
  9. customthe residue is chromatographed on AgNO3 -impregnated thin layer plates

Sources & evidence

ORD record
ord-3ae95931c5a44bfea2f1b3d1d5b90622
Source dataset
uspto-grants-1980_08
Patent number
US04217288

Reaction notes

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