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

HRID 25784

Reaktionsgleichung

Reaktionsgleichung von HRID 25784
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]([O:28][CH2:29]/[CH:30]=[CH:31]/[CH3:32])[CH3:27])=[CH:10][C:9]1([CH3:34])[CH3:33])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:29]([O:28][CH:26]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])[CH:13]=2)[NH:8][C:9]([CH3:34])([CH3:33])[CH:10]=1)[CH3:27])/[CH:30]=[CH:31]/[CH3:32]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 207603314-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 58 mg of [4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester in 2 mL of methylene chloride was treated with 0.05 mL of 99% trifluoroacetic acid (TFA) at room temperature. The reaction mixture was allowed to stir at the same temperature for 1 hour. TLC showed starting material was still remaining so another 0.05 mL of TFA was added. Ten minutes later, the reaction was quenched with water and extracted with EtOAc three times. The organic layers were combined, washed sequentially with water, saturated aqueous sodium bicarbonate, water, brine, dried with magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 28 mg of the title compound as an oil.

Aufarbeitung

  1. additionwas added
  2. customTen minutes later, the reaction was quenched with water
  3. extractionextracted with EtOAc three times
  4. washwashed sequentially with water, saturated aqueous sodium bicarbonate, water, brine
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1ea488f2001a4e0ea6289d4fd9ea2e95
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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