Toluene → HCID 59859868, Verbindung

HRID 1944555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944555
C(O[C:4](=[O:17])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)C.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C[Al](C)C.C1(C)C=CC=CC=1>ClCCCl.C(OCC)C.CO>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:4](=[O:17])[C:5]#[C:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:11][CH:12]=2)[CH:20]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 113753-AminoquinolineHCID 11333698Ethyl 3-(4-tert-Butylphenyl)propiolateHCID 16682925Trimethylaluminum

Produkt 1

HCID 59859868HCID 59859868, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of (4-tert-butyl-phenyl)-propynoic acid ethyl ester (0.23 g, 1.0 mmol) and 3-aminoquinoline (0.144 g, 1.0 mmol) in 1,2-dichloroethane (15 mL) was treated with a 2N solution of trimethylaluminum in toluene (0.75 mL, 1.5 mmol). The resultant solution was stirred at room temperature for 15 minutes, then heated at reflux for 18 h. The solution was cooled and treated with methanol (0.50 mL). The product was preabsorbed onto silica gel and purified by flash chromatography, using a gradient of methanol in dichloromethane as the eluant. The product was isolated, after trituration in diethyl ether, as a colorless solid, 0.17 g (52%). MS: m/z 329.2 (MH+). 1HNMR (DMSO-d6): δ 1.31 (s, 9 H), 7.54-7.72 (m, 6 H), 7.97 (d, 1 H), 8.72 (d, 1 H), 8.96 (d, 1 H) and 11.3 (s, 1 H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. temperatureThe solution was cooled
  4. customThe product was preabsorbed onto silica gel
  5. custompurified by flash chromatography
  6. customThe product was isolated

Quellen und Nachweise

ORD-Eintrag
ord-9e4bdf28025f4464bccd7795c172fc72
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394828B2

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