Tetrabutylammonium Fluoride → 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one

HRID 5338Notes

Reaction equation

HRID 5338 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[C:30][Si](C)(C)C)[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[CH:30])[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1462340011beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one

Product 1

HCID 1462340211beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-oneYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

470 mg of 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one in 24 ml of tetrahydrofuran is mixed with 2.35 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and stirred for 5 minutes at room temperature. It is poured on water and extracted with ethyl acetate. The combined organic phases are washed with water, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel. 280 mg of the title compound is isolated as foam.

Workup

  1. additionIt is poured on water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

Sources & evidence

ORD record
ord-5496bc558f464336aaaccae32ef16785
Source dataset
uspto-grants-1993_09
Patent number
US05244886

Reaction notes

Loading…