Dimethyl Sulfoxide → 4-(3-Methylisoxazol-5-yl)-butyraldehyde

HRID 1458353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458353
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[O:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl.[Cl-].[Na+].O>[CH3:11][C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][CH:20]=[O:21])[O:14][N:13]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221009164-(3-Methylisoxazol-5-yl)butan-1-ol

Produkt 1

HCID 221009094-(3-Methylisoxazol-5-yl)-butyraldehydeAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of oxalyl chloride (0.40 mL of a 2M solution in methylene chloride in 2 mL dry methylene chloride) at -78° C. was added a solution of methyl sulfoxide (126 mg in 1 mL methylene chloride) and the mixture stirred at low temperature for 3 minutes. A solution of 4-(3-methylisoxazol-5-yl)-butan-1-ol (100 mg in 1 mL methylene chloride) was added and the reaction allowed to proceed for 15 minutes after which time 0.67 mL triethylamine were added and the mixture allowed to warm to room temperature. After 30 minutes brine was added and the mixture extracted with methylene chloride. The organic portion was dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) gave the title compound (48 mg).

Aufarbeitung

  1. waitto proceed for 15 minutes
  2. extractionthe mixture extracted with methylene chloride
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica gel (ethyl acetate:hexane, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7e895af800934fbab7f031d69196731e
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849764

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