Sodium hydride → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(4-triethylsilyloxy-4-methylpentyloxymethyl)androsta-5,7,16-triene

HRID 1792170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792170
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.Br[CH2:56][CH2:57][CH2:58][C:59]([CH3:69])([O:61][Si:62]([CH2:67][CH3:68])([CH2:65][CH3:66])[CH2:63][CH3:64])[CH3:60]>O1CCCC1.C(OCC)(=O)C.O>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28][O:29][CH2:56][CH2:57][CH2:58][C:59]([O:61][Si:62]([CH2:67][CH3:68])([CH2:63][CH3:64])[CH2:65][CH3:66])([CH3:60])[CH3:69])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 220168021-Bromo-4-methyl-4-triethylsilyloxypentaneHCID 673014381alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

Produkt 1

HCID 696308821alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(4-triethylsilyloxy-4-methylpentyloxymethyl)androsta-5,7,16-trieneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (200 mg, 0.367 mmol), sodium hydride (60% in oil, 45 mg, 1.125 mmol) and 15-crown-5 (80 mg, 0.363 mmol) in tetrahydrofuran (1 ml), was added 1-bromo-4-methyl-4-(triethylsilyloxy)pentane (220 mg, 0.745 mmol) at room temperature, followed by reflux under heating for 1 hour. The reaction solution was diluted with ethyl acetate, followed by the dropwise addition of water under cooling with ice and washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the thus obtained residue was purified by column chromatography (hexane:ethyl acetate=15:1) to give the titled compound (278.7 mg, quant.) as a colorless oil.

Aufarbeitung

  1. temperatureby reflux
  2. temperatureunder heating for 1 hour
  3. temperatureunder cooling with ice
  4. washwashing with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe thus obtained residue was purified by column chromatography (hexane:ethyl acetate=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-9cc781dd66fd4b36b6a7e6f6c86e2e78
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074777B2

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