Tetrahydrofuran → HCID 70626539, compound

HRID 1834200Notes

Reaction equation

HRID 1834200 reaction equation
[O:1]1[CH:3]2[C:4](=[O:30])[CH2:5][CH:6]3[C@:27]([CH3:28])([CH:2]12)[C@@H:26]1[C@H:9]([C@H:10]2[C@:23]([CH3:29])([CH2:24][CH2:25]1)[C@@H:13]([C:14]([CH3:22])=[CH:15][CH:16]=[CH:17][C:18]([F:21])([CH3:20])[CH3:19])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)(=O)C>[F:21][C:18]([CH2:17][CH2:16][CH2:15][C@H:14]([C@@H:13]1[C@:23]2([CH3:29])[C@H:10]([C@H:9]3[C@H:26]([CH2:25][CH2:24]2)[C@:27]2([CH3:28])[C:6](=[CH:5][C@@H:4]([OH:30])[CH2:3][C@@H:2]2[OH:1])[CH:7]=[CH:8]3)[CH2:11][CH2:12]1)[CH3:22])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 86735381HCID 86735381, compound

Product 1

HCID 70626539HCID 70626539, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,2-Epoxy-25-fluorocholestadien-3-one (0.01 mole) prepared according to 3A above is dissolved in 100 ml. of dry tetrahydrofuran under a nitrogen blanket at 0° C. and fresh lithium aluminum hydride (0.005 mole) is slowly added over 10 minutes with stirring. The mixture is stirred for 1.0 hour and 1.0 ml. of ethyl acetate is added to destroy the excess lithium aluminum hydride. Concentrated aqueous ammonium chloride (20 ml.) is added to the reaction mixture and the mixture is stirred for 5 minutes. Diethyl ether (200 ml.) is added to the reaction mixture, the mixture is well shaken and the organic layer separated. The organic layer is washed with water, dried with magnesium sulfate and the solvent is evaporated to give crude 25-fluoro-4,6-cholestadiene-1α,3β-diol. 25-Fluoro-4,6-cholestadiene-1α,3β-diol can be purified by chromatographing the crude product on a silica gel column using a solvent of petroleum ether and diethyl ether.

Workup

  1. dissolutionabove is dissolved in 100 ml
  2. stirringThe mixture is stirred for 1.0 hour
  3. customto destroy the excess lithium aluminum hydride
  4. additionConcentrated aqueous ammonium chloride (20 ml.) is added to the reaction mixture
  5. stirringthe mixture is stirred for 5 minutes
  6. additionDiethyl ether (200 ml.) is added to the reaction mixture
  7. stirringthe mixture is well shaken
  8. customthe organic layer separated
  9. washThe organic layer is washed with water
  10. dry with materialdried with magnesium sulfate
  11. customthe solvent is evaporated

Sources & evidence

ORD record
ord-3e632303631c475bb0d90ac887a3c052
Source dataset
uspto-grants-1978_01
Patent number
US04069321

Reaction notes

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