Dimethyl Sulfoxide → 2-(3-Chloropyridin-2-yl)propanal

HRID 661375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661375
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:13]([CH:18]([CH3:21])[CH2:19][OH:20])=[N:14][CH:15]=[CH:16][CH:17]=1>C(Cl)Cl>[Cl:11][C:12]1[C:13]([CH:18]([CH3:21])[CH:19]=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 674994232-(3-Chloropyridin-2-yl)propan-1-ol

Produkt 1

HCID 866302832-(3-Chloropyridin-2-yl)propanalAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a −78° C. solution of dimethylsulfoxide (4.04 g, 3.67 mL, 51.7 mmol) in methylene chloride (25 mL) was added a solution of oxalyl chloride (3.28 g, 2.26 mL, 25.9 mmol) in methylene chloride (5 mL) over two minutes. The reaction mixture was stirred for 15 minutes, and then a solution of the product of Example 38C (0.74 g, 4.31 mmol) in methylene chloride (25 mL) was added over 8 minutes. The reaction was allowed to warm to ambient temperature and quenched with water. The quenched reaction mixture was extracted with methylene chloride, and the organic layer washed with brine and concentrated. The residue was chromatographed on silica gel eluting with 25% ethyl acetate-hexane to give the title compound (0.71 g, 97%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.73 (s, 1H), 8.53 (dd, J=1.5, 4.7, 1H), 8.00 (dd, J=1.4, 8.1, 1H), 7.40 (dd, J=4.7, 8.1, 1H), 4.28 (q, J=7.0, 1H), 1.34 (d, J=7.0, 3H). MS (DCI) m/z 170 (M+H)+.

Aufarbeitung

  1. customquenched with water
  2. customThe quenched reaction mixture
  3. extractionwas extracted with methylene chloride
  4. washthe organic layer washed with brine
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 25% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-8259ce4a410a4e28bd65424abeab5328
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084616B2

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