Sodium hydride → 11beta-[4-[2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethoxy]ethoxy]phenyl]estra-4,9-diene-3,17-dione

HRID 1358882Notes

Reaction equation

HRID 1358882 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:39][C@@:37]3([CH3:38])[C@@H:33]([CH2:34][CH2:35][C:36]3=[O:40])[C@H:32]3[C:23]2=[C:24]2[C:29]([CH2:30][CH2:31]3)=[CH:28][C:27](=[O:41])[CH2:26][CH2:25]2)=[CH:18][CH:17]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:12][C:11]([Si:8]([CH3:10])([CH3:9])[O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]2[CH2:39][C@@:37]3([CH3:38])[C@@H:33]([CH2:34][CH2:35][C:36]3=[O:40])[C@H:32]3[C:23]2=[C:24]2[C:29]([CH2:30][CH2:31]3)=[CH:28][C:27](=[O:41])[CH2:26][CH2:25]2)=[CH:20][CH:21]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1535193211beta-(4-Hydroxyphenyl)4,9-estra-diene-3,17-dioneHCID 18185637(2-(2-Bromoethoxy)ethoxy)(tert-butyl)dimethylsilane

Product 1

HCID 7001786611beta-[4-[2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethoxy]ethoxy]phenyl]estra-4,9-diene-3,17-dioneYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

412 mg of the product obtained in Stage B in solution in 2 cm3 of dimethylformamide is added to 362 mg of a mixture containing 362 mg of 11beta-(4-hydroxyphenyl)4,9-estra-diene-3,17-dione, 4 cm3 of dimethylformamide and 55 mg of sodium hydride. Agitation is carried out for 3 hours at ambient temperature, an aqueous solution of ammonium chloride is added, followed by extraction with ethyl acetate, washing with salt water, drying and evaporating the solvent. After chromatography on silica (eluant: ethyl acetate-essence G 6-4), 400 mg of expected product is obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with salt water
  3. customdrying
  4. customevaporating the solvent

Sources & evidence

ORD record
ord-c8a6c5c2c6aa43678891bb1284b295a3
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

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