Sodium hydride → HCID 86760144, compound

HRID 1792187Notes

Reaction equation

HRID 1792187 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:30]2([CH3:31])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:32])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([OH:25])([CH2:23][CH3:24])[CH3:22])[CH2:12][C@@H:11]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br/[CH:42]=[CH:43]\[CH2:44][C:45]([O:48][Si:49]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:50][CH3:51])([CH3:47])[CH3:46].[H-].[Na+].C1OCCOCCOCCOCCOC1>O1CCCC1>[Si:1]([O:8][C@@H:9]1[C@@:30]2([CH3:31])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:32])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:25]/[CH:42]=[CH:43]\[CH2:44][C:45]([O:48][Si:49]([CH2:50][CH3:51])([CH2:52][CH3:53])[CH2:54][CH3:55])([CH3:46])[CH3:47])([CH2:23][CH3:24])[CH3:22])[CH2:12][C@@H:11]([O:33][Si:34]([C:37]([CH3:39])([CH3:38])[CH3:40])([CH3:35])[CH3:36])[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 69629689HCID 69629689, compoundHCID 86760145HCID 86760145, compound

Product 1

HCID 86760144HCID 86760144, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-hydroxy-20-ethylpregna-5,7,16-triene (103 mg, 0.180 mmol), 1-bromo-4-triethylsilyloxy-4-methyl-(2Z)-pentene (211 mg, 0.719 mol), sodium hydride (60% in oil, 43 mg, 1.08 mmol), 15-crown-5 (40 mg, 0.182 mmol) and tetrahydrofuran (3 ml) were subjected to reaction using a procedure similar to that of Example 5(1) (reflux under heating for 1 hour), worked up and purified by column chromatography (hexane:toluene=1:1) to give the titled compound (141 mg, 100%) as a colorless solid.

Workup

  1. temperatureof Example 5(1) (reflux under heating for 1 hour)
  2. custompurified by column chromatography (hexane:toluene=1:1)

Sources & evidence

ORD record
ord-d3e80b1865d34207a9241eaeb472ffcb
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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