Sodium Methoxide → HCID 70565561, compound

HRID 2286322Notes

Reaction equation

HRID 2286322 reaction equation
Cl[C:2]1[CH2:7][C@H:6]2[C@H:8]3[C@:18]([F:22])([C@@H:19]([OH:21])[CH2:20][C@:4]2([CH3:5])[C:3]=1[S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]1)[CH2:10][CH2:9]3.[CH3:29][O-:30].[Na+]>CO>[CH2:27]([S:24]([C:3]1[C@:4]2([CH2:20][C@H:19]([OH:21])[C@@:18]3([F:22])[C@@H:8]([CH2:9][CH2:10][C:11]4[C@:16]3([CH3:17])[CH:15]=[CH:14][C:13](=[O:23])[CH:12]=4)[C@@H:6]2[CH2:7][C:2]=1[O:30][CH3:29])[CH3:5])(=[O:26])=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 70564043HCID 70564043, compound

Product 1

HCID 70565561HCID 70565561, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (11β)-16-chloro-17-(ethylsulfonyl)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one (1.29 g; prepared as described above) in anhydrous methanol (190 ml) containing sodium methoxide (800 mg) is refluxed for 3 hours. The resulting solution is concentrated in vacuo, diluted with water, saturated with sodium chloride and extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried (anhydrous Na2SO4) and evaporated to afford the crude material (1.2 g). This is chromatographed over silica gel (60 g) to isolate the title compound (505 mg), melting point 288°-289° C., after crystallization from acetone-hexane.

Workup

  1. temperatureis refluxed for 3 hours
  2. concentrationThe resulting solution is concentrated in vacuo
  3. additiondiluted with water, saturated with sodium chloride
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washis washed with water
  7. dry with materialdried (anhydrous Na2SO4)
  8. customevaporated
  9. customto afford the crude material (1.2 g)
  10. customThis is chromatographed over silica gel (60 g)

Sources & evidence

ORD record
ord-078deeb0dcf84b8f95dfc448c7253322
Source dataset
uspto-grants-1981_05
Patent number
US04265815

Reaction notes

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