HCID 13145956, compound → HCID 22823201, compound

HRID 851291Notes

Reaction equation

HRID 851291 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[F:7][C@@H:8]1[C:25]2[C@:20]([CH3:27])([CH2:21][CH2:22][C:23](=[O:26])[CH:24]=2)[C:19]2[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH:18]=2)([CH3:16])[C:14](=[O:28])[CH2:13][CH2:12]3)[CH2:9]1>C1COCC1>[C:1]([C@:14]1([OH:28])[CH2:13][CH2:12][C@H:11]2[C@H:10]3[C:19](=[CH:18][CH2:17][C@:15]12[CH3:16])[C@:20]1([CH3:27])[C:25]([CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)=[C:8]([F:7])[CH2:9]3)#[CH:2]

Participants

4

Reactant 2

HCID 13145956HCID 13145956, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22823201HCID 22823201, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium t-butoxide (as a 20% solution in THF, 1.6 ml) is added to THF (10 ml) containing 6α-fluoro-androst-4,9(11)-diene-3,17-dione (V, Example 4, 350 mg), previously cooled to -10°. After stirring at -10° for 40 min, acetylene is slowly bubbled in over 2 hrs. The solution is then allowed to warm to 20°-25°, quenched with aqueous ammonium chloride and extracted with ethyl acetate which is then back extracted with water, dried over sodium sulfate, the solvent removed under reduced pressure to give the title compound Rf (ethyl acetate/hexane, 1/1)=0.6; NMR (CDCl3 +CD3OD) 0.9, 1.4, 2.6 and 5.7 δ.

Workup

  1. temperaturepreviously cooled to -10°
  2. customacetylene is slowly bubbled in over 2 hrs
  3. temperatureto warm to 20°-25°
  4. customquenched with aqueous ammonium chloride
  5. extractionextracted with ethyl acetate which
  6. extractionis then back extracted with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-42c919c5238842b6beaa3f0f962fa7e4
Source dataset
uspto-grants-1983_05
Patent number
US04383947

Reaction notes

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