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

HRID 651506ノート

反応式

HRID 651506 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-99d74e21d56643bf86d95479ab9e85b0
出典データセット
uspto-grants-2001_08
特許番号
US06281204B1

反応ノート

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