Hydrochloric Acid → 6-Methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde

HRID 1159783ノート

反応式

HRID 1159783 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:5]([CH:21]=C)[CH:4]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:32].[Na+].Cl>O1CCOCC1.O.[Os](=O)(=O)(=O)=O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[O:32])[C:6]2[CH:7]=[CH:8][N:9]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:13])=[O:14])[C:10]=2[CH:11]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687171136-Methoxy-1-(phenylsulfonyl)-4-vinyl-1H-indole2 回

生成物 1

HCID 866182416-Methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde収率 144.5%

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

6-Methoxy-1-(phenylsulfonyl)-4-vinyl-1H-indole (0.27 g, 0.9 mmol; Intermediate 33) was dissolved in dioxane (24 mL) and 2,6-lutidine (0.2 mL, 1.7 mmol) was added. Osmium tetraoxide (0.011 g, 0.04 mmol) was added and after 15 min of stirring did the mixture change colour to black. Sodium periodate (0.74 g, 3.4 mmol) dissolved in water (8 mL, warmed to dissolve) was added and a precipitation started to form. After 1 h of stirring at rt was the mixture portioned between 2N HCl and dichloromethane. The organic layer was dried (Na2SO4) and concentrated to give 0.41 g of the crude product. MS (ESI+) for C16H13NO4S m/z 316 (M+H)+.

後処理

  1. additionwas added
  2. customa precipitation
  3. customto form
  4. stirringAfter 1 h of stirring at rt
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-53e9b624730e4a739bdcd7d9ec33d7e0
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

反応ノート

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