Chloroform → Ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate

HRID 1066228ノート

反応式

HRID 1066228 の反応式
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]2[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:4]=12.P(Cl)(Cl)(Cl)=O.[CH:23]([Cl:26])(Cl)Cl>CN(C)C=O>[Cl:26][C:23]1[C:4]2[C:5](=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:7][C:3]=2[S:2][CH3:1])[CH2:13][CH2:14][C:15]=1[CH:16]=[O:17]

参加物

5

反応物 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 2778748Ethyl 3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

生成物 1

HCID 2778781Ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate収率 73.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (5.47 g) was dissolved in chloroform (130 ml) and added dropwise to a solution of phosphorus oxychloride (50.71 g) in N,N-dimethylformamide (40 ml) at 0° C. This mixture was stirred at room temperature, after which it was refluxed under heating in a nitrogen stream for 4.5 hours. The reaction mixture was poured over ice water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate (4.72 g, 73.8%), which was then recrystallized from ethyl acetate. Yellow prisms. Melting point 79-80° C.

後処理

  1. temperatureafter which it was refluxed
  2. temperatureunder heating in a nitrogen stream for 4.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off

出典と根拠

ORDレコード
ord-6159bcdeaad54808bdf0620c4b2581a8
出典データセット
uspto-grants-2001_06
特許番号
US06242471B1

反応ノート

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