Chloroform → HCID 70400495, compound

HRID 371055Notes

Reaction equation

HRID 371055 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@H:19]2[S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:15]2[C@@:6]1([F:32])[C@:7]1([CH3:31])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:30])[CH:9]=[CH:8]1)(=O)C.[OH-].[Na+].C(Cl)(Cl)Cl.C(OCC)(=O)C>O1CCCC1.CO>[F:32][C@:6]12[C@@H:5]([OH:4])[CH2:22][C@@:20]3([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@H:19]3[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:15]1[CH2:14][CH2:13][C:12]1[C@:7]2([CH3:31])[CH:8]=[CH:9][C:10](=[O:30])[CH:11]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70400272HCID 70400272, compound

Product 1

HCID 70400495HCID 70400495, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (11β,17α)-11-(acetyloxy)-9-fluoro-17-(phenylthio)androsta-1,4-dien-3-one (300 mg) in tetrahydrofuran (12.0 ml) and methanol (6.0 ml) (in a nitrogen atmosphere) was added 1.5 ml of a 12% sodium hydroxide solution. TLC (7:3, chloroform:ethyl acetate) taken after 1 hour showed the reaction to be complete. After a total of 1.5 hours at room temperature, the reaction was quenched with water and extracted with chloroform (3×50 ml). The chloroform extracts were pooled, dried over anhydrous magnesium sulfate and evaporated to a yellow oil. This was dissolved in 10.0 ml of boiling dichloromethane, cooled, and a few drops of petroleum ether were added. The solution was left in the freezer overnight, yielding fine, light green needle-like crystals (57 mg) of an analytical specimen with consistent spectral data and melting point 248°-252° C. (with decomposition).

Workup

  1. customthe reaction
  2. customAfter a total of 1.5 hours at room temperature, the reaction was quenched with water
  3. extractionextracted with chloroform (3×50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to a yellow oil
  6. dissolutionThis was dissolved in 10.0 ml of boiling dichloromethane
  7. temperaturecooled
  8. additiona few drops of petroleum ether were added
  9. customyielding fine

Sources & evidence

ORD record
ord-26ba223b94de41d2a9a7c36ab6bf6634
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

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