Sodium hydride → HCID 67226237, compound

HRID 624332Notes

Reaction equation

HRID 624332 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 (9812 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 (9812 ethyl acetate, hexanes)

Sources & evidence

ORD record
ord-5d1b7829c65f4848976e219b18b8e82f
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

Loading…