2,6-Lutidine → 1-Tosyl-1H-indole-4-carbaldehyde

HRID 1159754

Reaction equation

HRID 1159754 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([CH:20]=C)[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:31])[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 124465911-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole2×HCID 23667635Sodium periodate

Product 1

HCID 131150931-Tosyl-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

OsO4 (6 mg, 0.023 mmol) was added to a stirred mixture of 1-[(4-methylphenyl)sulfonyl]-4-vinyl-1H-indole (68 mg, 0.23 mmol; Intermediate 4) and 2,6-lutidine (54 μL, 0.46 mmol) in dioxane (6 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.197 g, 0.92 mmol) in water (1.5 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 20 min. and partitioned between 2M aqueous HCl (25 mL) and DCM (25 mL). The organic layer was dried, filtered and combined with Intermediate 5 batch 2.

Workup

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. custompartitioned between 2M aqueous HCl (25 mL) and DCM (25 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6975bbe82eba42e4a72b4b46ff4c6e5e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Linked notes

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