Indole → 1-(dimethyl-t-butylsilyl)indole

HRID 1798019Notes

Reaction equation

HRID 1798019 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[Na]N1C2C(=CC=CC=2)C=C1.[CH3:22][Si:23](Cl)([CH3:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1>[CH3:22][Si:23]([CH3:28])([C:24]([CH3:27])([CH3:26])[CH3:25])[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 798IndoleHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178507088HCID 178507088, compound

Product 1

HCID 100600911-(dimethyl-t-butylsilyl)indoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(dimethyl-t-butylsilyl)indole is prepared by treatment of indole with sodium hydride in THF at temperature followed by the reaction of 1-sodioindole with dimethyl-t-butylsilyl chloride in THF according to the procedure described in D. Dhanak, C. B. Reese J. Chem. Soc., Perkin Trans. 1 1986, 2181-2186. The yield is 79%. The physical and spectral characteristics are described in this article.

Sources & evidence

ORD record
ord-6f1a8fdc0dc247f4abc79d549a30fd69
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

Loading…