Dimethylformamide → HCID 18472473、化合物

HRID 2228216ノート

反応式

HRID 2228216 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C=O)C>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:19])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 18472193HCID 18472193、化合物

生成物 1

HCID 18472473HCID 18472473、化合物収率 85.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen atmosphere, to a solution of 5-[5—(4-methylphenyl)thiophen-2-yl]valeric acid (2.60 g) in tetrahydrofuran (30 ml) was added oxalyl chloride,(1.24 ml) at room temperature and then a drop of DMF, and the mixture was stirred 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dichloromethane(30 ml). To the mixture was added tin tetra-chloride (1.5 ml) at 0° C., and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to water to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane:=1:9→1:5) to give 2—(4-methylphenyl)-4-oxo-5,6,7,8-tetrahydro-4H-cyclo-hepta[b]thiophene (2.07 g) as pale yellow crystals.

後処理

  1. customUnder reduced pressure, the solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane(30 ml)
  3. additionTo the mixture was added tin tetra-chloride (1.5 ml) at 0° C.
  4. additionThe reaction mixture was added to water
  5. customthe reaction
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was separated
  11. custompurified with column chromatography (ethyl acetate/hexane:=1:9→1:5)

出典と根拠

ORDレコード
ord-f5dd77d5177249169ace49b2f4a1e0d1
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

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