Sodium hydride → HCID 67226237, compound

HRID 1848810Notes

Reaction equation

HRID 1848810 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)C1C=CC=CC=1.[H-].[Na+].[CH:20]([Si:23](Cl)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21]>C1COCC1>[CH:20]([Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:9]([OH:8])[C:10]=2[CH:11]=[CH:12]1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 884654-(phenylmethoxy)-1H-indoleHCID 139400Triisopropylsilyl chloride

Product 1

HCID 67226237HCID 67226237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxyindole (1 g) was treated with 60% oily NaH (135 mg) and triisopropylsilyl chloride (1 g) in THF, purified by flash chromatography (98/2 ethyl acetate/hexanes), then debenzylated in ethanol (35 mL) using Pearlman's catalyst (0.19 g) and a hydrogen balloon.

Workup

  1. custompurified by flash chromatography (98/2 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ebdbcacc85b04b9eb3ffd298fcb26074
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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