HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium bis(trimethylsilyl)amide → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | 6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester | HCID 69153727 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 2-Butene, 1-bromo-3-methyl- | HCID 70092 | — |
| Product | 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline | HCID 10316670 | 32.7% |
Reaction Steps
6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (96 mg) was treated with 450 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 50 μL of 4-bromo-2-methyl-2-butene to give the alkylated product, which was deprotected to yield 14.5 mg of the 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-d5f249d5ca93471aaf3c153cf810d56a |
| Source note | uspto-grants-2005_02 |