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-phenethyloxyethyl)-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester | HCID 69152501 | — |
| Solvent | Phenethyl bromide | HCID 7666 | — |
| 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 | 140.4% |
Reaction Steps
6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (100 mg) was treated with 360 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 45 μL of phenethyl bromide to give the alkylated product, which was deprotected to yield 62 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-f7d5dd04ee0f424a9cdb3a8acaf6d5c2 |
| Source note | uspto-grants-2005_02 |