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Water → 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25781
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 25781
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH3:21].[Li]CCCC.[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28].O>C(Cl)Cl.CCCCCC>[C:27]([O:31][C:32]([N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:18][CH:17]=2)[C:12]([CH3:21])=[CH:13][C:14]1([CH3:20])[CH3:19])=[O:33])([CH3:30])([CH3:29])[CH3:28]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 225665156-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineHCID 178418339Butyllithium

Produkt 1

HCID 207603346-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A mixture of 2.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (see Example 1) in 35 mL of CH2Cl2 was cooled down to −78° C. To this mixture, 13.1 mL of 1.6 M n-BuLi in hexane was added dropwise. The mixture was warmed to 0° C. and 2.9 g of (di-tert-butyl)carbonate was added. The mixture was allowed to stir at 0° C. for 1 hour. The reaction was then worked up by adding water and extracting with EtOAc three times. The organic layers were combined, washed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution, dried over magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 1.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

Aufarbeitung

  1. temperatureThe mixture was warmed to 0° C.
  2. extractionextracting with EtOAc three times
  3. washwashed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f8bf4aae3f14dbab3f2ec3865b2b222
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06858627B2

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