Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2406677Generated: October 26, 2026

Lithium Hexamethyldisilazide → 5-Chloro-2-(5-methyl-hex-1-enyl)-1H-indole

https://huagongshe.com/reaction/2406677

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium HexamethyldisilazideHCID 2733832—
ReactantPhosphonium, (4-methylpentyl)triphenyl-, bromideHCID 10928070—
Reactant5-Chloro-1H-indole-2-carbaldehydeHCID 12203318—
SolventTetrahydrofuranHCID 8028—
Product5-Chloro-2-(5-methyl-hex-1-enyl)-1H-indoleHCID 68751320—

Reaction Steps

To the cold suspension of (4-methyl-pentyl)-triphenyl-phosphonium bromide in THF was added LiHMDS in THF and the mixture was stirred for 30 minutes and then the solution of 5-chloro-1H-indole-2-carbaldehyde was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product, 5-chloro-2-(5-methyl-hex-1-enyl)-1H-indole was purified by column chromatography.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08809382B2
Source datasetuspto-grants-2014_08
ORD IDord-d2a9e4774b46443698e45265323b5eef
Source noteuspto-grants-2014_08