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

HRID 1159783노트

반응식

HRID 1159783 반응식
[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

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 687171136-Methoxy-1-(phenylsulfonyl)-4-vinyl-1H-indole2회

생성물 1

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

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-53e9b624730e4a739bdcd7d9ec33d7e0
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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