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p-METHYLACETOPHENONE → 1-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol

HRID 1788370
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1788370
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH3:21])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([N-]C(C)C)(C)C.[Li+].[CH3:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:41])[CH3:40])=[CH:35][CH:34]=1>O1CCCC1.[Cl-].[Na+].O>[CH3:21][C:13]1[CH:12]=[C:11]([CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH2:1][C:39]([C:36]3[CH:37]=[CH:38][C:33]([CH3:32])=[CH:34][CH:35]=3)([OH:41])[CH3:40])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8500p-METHYLACETOPHENONEHCID 2724682Lithium diisopropylamideHCID 230180214-(4-Methanesulfonylphenoxymethyl)-2-methylquinoline

Produkt 1

HCID 230179531-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-olAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg (1.59 mmol) of p-methylacetophenone in tetrahydrofuran, followed by stirring for 2.5 hours. The reaction was stopped by the addition of saturated brine, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under a reduced pressure. The obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2) to obtain 440 mg (0.95 mmol) of 1-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol (VIII-57). Its physical property is shown below.

Aufarbeitung

  1. stirringby stirring for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-97adc6632ffe4899b931aa4034848e5d
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07511144B2

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