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

HRID 1108354
ノート
印刷プレビュー

反応式

HRID 1108354 の反応式
Cl[C:2]1[C:10]2[C:6](=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:8][C:9]=2[S:11][CH3:12])[CH2:5][CH2:4][C:3]=1[CH:18]=[O:19].C(N(CC)CC)C.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:28][SH:29]>N1C=CC=CC=1>[CH2:32]([O:31][C:27]([CH2:28][S:29][C:2]1[C:10]2[C:6](=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:8][C:9]=2[S:11][CH3:12])[CH2:5][CH2:4][C:3]=1[CH:18]=[O:19])=[O:30])[CH3:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 2778781Ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate

生成物 1

HCID 18388318Ethyl 4-ethoxycarbonylmethylthio-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a mixture of ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate (3.00 g), triethylamine (1.44 g) and pyridine (25 ml), ethyl thioglycolate (1.37 g) was added at 0° C., followed by stirring at 0° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure; the residue was poured over water and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and water in that order and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:7 to 1:5, v/v) to yield ethyl 4-ethoxycarbonylmethylthio-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate (3.07 g, 81.0%), which was then recrystallized from ethyl acetate-hexane. Yellow prisms. Melting point 102-103° C.

後処理

  1. additionwas added at 0° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured over water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with 1 N hydrochloric acid and water in that order
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off
  8. washeluted with ethyl acetate-hexane (1:7 to 1:5

出典と根拠

ORDレコード
ord-4c17657712284ba3a3dc67d3288f1d01
出典データセット
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06066658

反応ノート

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