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

HRID 653025

反応式

HRID 653025 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-429de137afae424e9bb51467401e8ed8
出典データセット
uspto-grants-1987_06
特許番号
US04675186

関連ノート

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