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

HRID 1792183Notes

Reaction equation

HRID 1792183 reaction equation
[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]([O:47][Si:48]([CH2:53][CH3:54])([CH2:51][CH3:52])[CH2:49][CH3:50])([CH3:46])[CH3:45].[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]([O:47][Si:48]([CH2:49][CH3:50])([CH2:51][CH3:52])[CH2:53][CH3:54])([CH3:45])[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]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 220276611-Bromo-4-methyl-4-triethylsilyloxy-2-pentyneHCID 696299251alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene

Product 1

HCID 696299631alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(4-triethylsilyloxy-4-methyl-2-pentynyloxy)-20-methylpregna-5,7,16-trieneYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-Butyldimethylsilyloxy)-20-hydroxy-20-methylpregna-5,7,16-triene (100 mg, 0.175 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-2-pentyne (203 mg, 0.697 mmol), sodium hydride (60% in oil, 42 mg, 1.05 mmol), 15-crown-5 (38 mg, 0.173 mmol) and tetrahydrofuran (3 ml) were reacted using a procedure similar to that of Example 5 (1) (reflux under heating for 17 hours), worked-up and purified by column chromatography (hexane:toluene=2:1) to give the titled compound (85 mg, 62%) as a colorless oil.

Workup

  1. custompurified by column chromatography (hexane:toluene=2:1)

Sources & evidence

ORD record
ord-7b246f45fa6645ec92d12a7f69d24d40
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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