Dimethyl Sulfoxide → 2-cyclopropylthiazole-4-carbaldehyde

HRID 532837Notes

Reaction equation

HRID 532837 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:10][CH2:9]2)[S:6][CH:7]=1.CS(C)=[O:13]>CCOC(C)=O.O=[Mn]=O>[CH:8]1([C:5]2[S:6][CH:7]=[C:3]([CH:2]=[O:13])[N:4]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 180714234-(chloromethyl)-2-cyclopropyl-1,3-thiazole

Product 1

HCID 457919582-cyclopropylthiazole-4-carbaldehydeYield 38%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(chloromethyl)-2-cyclopropylthiazole (3.0 g, 17.2 mmol) in DMSO (10 mL) was charged MnO2 (1.5 g, 17.2 mmol). The mixture was heated to 100° C. overnight, cooled to room temperature and diluted with EtOAc (30 mL). The mixture was filtered through Celite and washed with EtOAc (3×30 mL). The combined organic layer was washed with brine (3×40 mL) and concentrated. The residue was purified by silica gel chromatography using 2 to 5% EtOAc in hexane to afford the title compound (1.0 g, 38%) as a light brown oil, which solidified upon standing in a refrigerator overnight. 1H NMR (400 MHz, CDCl3) δ 9.91 (s, 1H), 7.93 (s, 1H), 2.36 (m, 1H), 1.20 (m, 2H), 1.16 (m, 2H). MS (ES) m/z 154.1 (M+H+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with EtOAc (3×30 mL)
  4. washThe combined organic layer was washed with brine (3×40 mL)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9058fec120884a6690966e36be8d8dbd
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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