Sodium hydride → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(4-ethyl-4-triethylsilyloxy-2-hexynyloxy)-20-methylpregna-5,7,16-triene

HRID 1792189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792189
[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([OH:24])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:41][C:42]#[C:43][C:44]([CH2:55][CH3:56])([O:47][Si:48]([CH2:53][CH3:54])([CH2:51][CH3:52])[CH2:49][CH3:50])[CH2:45][CH3:46].[H-].[Na+].C1OCCOCCOCCOCCOC1>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:29]2([CH3:30])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24][CH2:41][C:42]#[C:43][C:44]([CH2:55][CH3:56])([O:47][Si:48]([CH2:53][CH3:54])([CH2:49][CH3:50])[CH2:51][CH3:52])[CH2:45][CH3:46])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 220276881-Bromo-4-ethyl-4-triethylsilyloxy-2-hexyneHCID 696299251alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene

Produkt 1

HCID 696304481alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(4-ethyl-4-triethylsilyloxy-2-hexynyloxy)-20-methylpregna-5,7,16-trieneAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.17 mmol), 1-bromo-4-ethyl-4-triethylsilyloxy-2-hexyne (150 mg, 0.47 mmol), sodium hydride (60% in oil, 41 mg, 1.02 mmol), 15-crown-5 (37 mg, 0.17 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (at room temperature for 17 hours), worked up and purified by preparative thin layer chromatography (3 sheets (each 1.0 mm thickness), hexane:toluene=1:1) to give the titled compound (52 mg, 37.7%) as a yellow oil.

Aufarbeitung

  1. customof Example 5(1) (at room temperature for 17 hours)
  2. custompurified by preparative thin layer chromatography (3 sheets (each 1.0 mm thickness), hexane

Quellen und Nachweise

ORD-Eintrag
ord-4bbe192ac8e24825a0f792208891f093
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074777B2

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