Dimethyl Sulfoxide → Ethanone, 1-(2-furanyl)-2-(methylsulfinyl)-

HRID 653025

Reaction equation

HRID 653025 reaction equation
[CH3:1][S:2]([CH3:4])=[O:3].[H-].[Na+].C1COCC1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](OC)=[O:18]>O>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](=[O:18])[CH2:1][S:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8028TetrahydrofuranHCID 11902Methyl 2-furoateHCID 24758Sodium hydride

Product 1

HCID 200873Ethanone, 1-(2-furanyl)-2-(methylsulfinyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

DMSO (35 ml., dry, distilled from CaH2) and NaH (3.08 g., 0.076 mol as a 60% suspension in oil) was heated under nitrogen until evolution of H2 was complete, cooled to 0° C., and diluted with 35 ml. THF. Methyl furan-2-carboxylate (5 ml., 5.89 g., 0.047 mol) was added, the mixture warmed to ambient temperature, stirred 2 hours, poured into an equal volume of water, and extracted with one half volume of ether. The aqueous layer was adjusted to pH3 with 6N HCl and extracted 3×150 ml. CHCl3. The CHCl3 extracts were combined, dried and evaporated to an oil which crystallized on standing in vacuum. The latter was slurried in minimal 1:1 CHCl3 :hexane and recovered by filtration, 2.84 g.; tlc Rf 0.7 (3:1 ethyl acetate: methanol); 1H-nmr 2.75 (s, 3H), 4.21 (ABq, 2H), 6.58 (dd, 1H), 7.32 (d, 1H), 7.62 (d, 1H).

Workup

  1. additiondiluted with 35 ml
  2. temperaturethe mixture warmed to ambient temperature
  3. extractionextracted with one half volume of ether
  4. extractionextracted 3×150 ml
  5. customdried
  6. customevaporated to an oil which
  7. customcrystallized
  8. filtrationhexane and recovered by filtration, 2.84 g

Sources & evidence

ORD record
ord-429de137afae424e9bb51467401e8ed8
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Linked notes

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