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

HRID 1159783Notes

Reaction equation

HRID 1159783 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-53e9b624730e4a739bdcd7d9ec33d7e0
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…