Sodium Thiosulfate → HCID 57901786, compound

HRID 1851411Notes

Reaction equation

HRID 1851411 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][OH:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH:15]=[O:16]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57901683HCID 57901683, compound

Product 1

HCID 57901786HCID 57901786, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(1,3-thiazol-2-yl)-1H-indol-7-yl]methanol (0.610 g) in dichloromethane (50 mL) was added Dess-Martin oxidant (1.50 g), and the mixture was stirred at room temperature for 0.5 hr. the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution and 1N aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50) to give the title compound (0.450 g, yield 74%) as pale-yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50)

Sources & evidence

ORD record
ord-634d4c90d88c4a28970ddcc4a264eaf7
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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