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

HRID 34726

반응식

HRID 34726 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7227e10a3be6489cb74110c7559287ec
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762921

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