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Dimethyl Sulfoxide → methyl 1-allyl-3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate

HRID 1518252
ノート
印刷プレビュー

反応式

HRID 1518252 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[CH2:41][OH:42])[CH:12]=[CH2:13].CCN(CC)CC>C(Cl)Cl>[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[CH:41]=[O:42])[CH:12]=[CH2:13]
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

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67345867methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate

生成物 1

HCID 86627900methyl 1-allyl-3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate収率 88%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

反応条件

温度
-78 °C

実験手順

DMSO (5 eq.) was dissolved in DCM and the solution was cooled to −78° C. To the stirred solution oxalylchloride (2.5 eq.) was added and the mixture was left stirring for 30 min. A solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)-4-methoxyphenyl]-1H-indole-6-carboxylate (1 eq.) in DCM (0.25M solution) was added and the mixture was left stirring for 30 min at −78° C. Et3N (8 eq.) was added and the mixture was allowed to warm to 0° C. At this temperature stirring was continued for 2 h, and then stirring was continued at RT overnight. The mixture was diluted with DCM, and then washed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was purified by flash chromatography (PE:EtOAc, 9:1). After evaporation of the solvents the product was obtained as a yellow foam (88%). MS (ES+): 432.1 (M+H+).

後処理

  1. waitthe mixture was left
  2. waitthe mixture was left
  3. stirringstirring for 30 min at −78° C
  4. temperatureto warm to 0° C
  5. stirringAt this temperature stirring
  6. waitwas continued for 2 h
  7. stirringstirring
  8. waitwas continued at RT overnight
  9. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and with brine
  10. dry with materialAfter drying over Na2SO4 all volatiles
  11. customwere evaporated in vacuo
  12. customThe residual material was purified by flash chromatography (PE:EtOAc, 9:1)
  13. customAfter evaporation of the solvents the product

出典と根拠

ORDレコード
ord-ee30a91f0d7d42a9a9762bdc2d6de347
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08232390B2

反応ノート

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