Dimethyl Sulfoxide → 4-(7-Chloroquinolin-4-yl)butyraldehyde

HRID 1274409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274409
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([CH2:22][CH2:23][CH2:24][CH:25]=[O:26])=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 221206674-(7-Chloroquinolin-4-yl)butan-1-ol

Produkt 1

HCID 221206734-(7-Chloroquinolin-4-yl)butyraldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Oxalyl chloride (0.42 mL of a 2M solution in dry methylene chloride) was placed in an oven-dried flask, cooled to -78° C. and a solution of 99 mg methylsulfoxide in dry methylene chloride (2 mL) added drop by drop to the oxalyl chloride over 3 minutes and stirred for a further 3 minutes. A solution of 4-(7-chloroquinolin-4-yl)butan-1-ol (100 mg) in dry methylene chloride (1 mL) was added to the reaction flask over approx. 3 minutes followed by anhydrous triethylamine (0.42 mL) and the reaction mixture stirred for another 2.5 hours during which time it was allowed warmed up to room temperature. The reaction was quenched by the addition of saturated brine and then partitioned with methylene chloride. The aqueous layer was discarded and the methylene chloride extract dried over anhydrous sodium sulfate powder, filtered and concentrated in vacuo. The title compound was isolated by flash chromatography on silica gel (ethyl acetate:hexane, 2:1; then ethyl acetate), 57 mg.

Aufarbeitung

  1. stirringthe reaction mixture stirred for another 2.5 hours during which time it
  2. temperaturewas allowed warmed up to room temperature
  3. customThe reaction was quenched by the addition of saturated brine
  4. custompartitioned with methylene chloride
  5. extractionthe methylene chloride extract
  6. dry with materialdried over anhydrous sodium sulfate powder
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cb0d1846999c48b7b3ba7a03c6b96910
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156767

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