Tetrahydrofuran → HCID 86760158, compound

HRID 1792225Notes

Reaction equation

HRID 1792225 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[N:10]=[N:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:14]([O:21][C@@H:22]1[C@@:39]2([CH3:40])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:38]2[CH2:37][CH2:36][C@@:34]2([CH3:35])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[CH2:41][O:42]CCC(N(C)C)=O)[CH2:25][C@@H:24]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O1CCCC1.CC(C)([O-])C.[K+]>[Cl-].[Na+].O>[C:1]1([N:7]2[C:8](=[O:13])[N:9]=[N:10][C:11]2=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[Si:14]([O:21][C@@H:22]1[C@@:39]2([CH3:40])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:38]2[CH2:37][CH2:36][C@@:34]2([CH3:35])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[CH2:41][OH:42])[CH2:25][C@@H:24]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:52])[CH3:53])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 86589971HCID 86589971, compound

Product 1

HCID 86760158HCID 86760158, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(N,N-dimethylaminocarbonylethoxymethyl)androsta-5,7-diene 4-phenyl-1,2,4-triazoline-3,5-dione adduct (9 g), were added tetrahydrofuran (90 ml) and then potassium t-butoxide (10.5 g), followed by reaction at room temperature for 10 min. After stopping the reaction by adding saturated brine, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove the solvent and the thus obtained residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give the titled compound (6.34 g).

Workup

  1. customthe reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customthe thus obtained residue was purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5385123b715d4c92b06b49dff910a28e
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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