HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2-Bromoethyl)cyclohexane → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2-Bromoethyl)cyclohexane | HCID 15440 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | 4-[1-(2-Cyclohexylethoxy)ethyl]-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 | HCID 69153946 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline | HCID 10316670 | 101% |
Reaction Steps
4-[1-(2-Cyclohexylethoxy)ethyl]-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 49 mg of 2-cyclohexylethyl bromide to give the alkylated product, which was deprotected to yield 31 mg of title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06858627B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-ce9a7ee077a34850b30661c174215de3 |
| Source note | uspto-grants-2005_02 |