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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 25788Generated: October 26, 2026

Cyclohexane, (bromomethyl)- → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

https://huagongshe.com/reaction/25788

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyclohexane, (bromomethyl)-HCID 137636—
ReactantSodium bis(trimethylsilyl)amideHCID 2724254—
Reactant4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterHCID 69190771—
SolventTetrahydrofuranHCID 8028—
Product4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineHCID 1031667025.6%

Reaction Steps

4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 45 mg of cyclohexylmethyl bromide to give the alkylated product, which was deprotected to yield 8 mg of the title compound as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06858627B2
Source datasetuspto-grants-2005_02
ORD IDord-44529c863784495ba0268ab73cd417bc
Source noteuspto-grants-2005_02