Sodium hydride → HCID 86614880, compound

HRID 549500Notes

Reaction equation

HRID 549500 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][C:14]2[CH:13]=[CH:12][C:11]([CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])=[CH:10][C:9]3=2)[CH2:3][CH2:2]1.[H-].[Na+].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C1COCC1>[C:30]([Si:27]([O:23][C:21]([CH3:24])([CH3:22])[CH2:20][C:11]1[CH:12]=[CH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:8]([C:9]=2[CH:10]=1)=[CH:7][C:6]([O:5][CH2:4][CH:1]1[CH2:2][CH2:3]1)=[CH:19][CH:18]=3)([CH3:29])[CH3:28])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 86614881HCID 86614881, compound

Product 1

HCID 86614880HCID 86614880, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 1-[6-(cyclopropylmethoxy)-3-phenanthryl]-2-methylpropan-2-ol from Step 4 above in THF (10 mL), was added sodium hydride (60% dispersion in oil, 0.27 g, 6.79 mmol). The mixture was heated at reflux for 2 minutes, then cooled to room temperature. Tert-butyldimethylsilylchloride (0.512 g, 3.39 mmol) was added and the reaction mixture heated at reflux for 2 h. After usual workup of the reaction, tert-butyl(2-[6-(cyclopropylmethoxy)-3-phenanthryl]-1,1-dimethylethoxy)dimethylsilane (0.5 g) was obtained, which was used as crude material for the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 minutes
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux for 2 h
  5. customAfter usual workup of the reaction

Sources & evidence

ORD record
ord-08fbf545786b449f8e0db4099d54a729
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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