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Dimethyl Sulfoxide → Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

HRID 1518257
ノート
印刷プレビュー

反応式

HRID 1518257 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=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][CH:36]=[CH:35][C:34]=1[CH2:39][OH:40])[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][CH:36]=[CH:35][C:34]=1[CH:39]=[O:40])[CH:12]=[CH2:13]
参加物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 68702775Methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

生成物 1

HCID 86637858Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
3 回

実験手順

Oxalyl chloride (2.5 eq., 2M solution in DCM) was added at −70° C. under nitrogen atmosphere to a solution of DMSO (5 eq.) in anhydrous DCM and the mixture was stirred for 30 min; a solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate in DCM was then added and stirring was continued at the same temperature for 30 min. before NEt3 (8 eq.) was added. After stirring for 20 min. at 0° C. the mixture was diluted with DCM, then washed with water, 1N HCl, saturated aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was used in the next step without purification. MS (ES+): 402.2 (M+H+).

後処理

  1. stirringstirring
  2. additionwas added
  3. stirringAfter stirring for 20 min. at 0° C. the mixture
  4. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residual material was used in the next step without purification

出典と根拠

ORDレコード
ord-1763e5c80cc94d4d83d1e3aa9dc0335c
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

読み込み中…

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