Water → HCID 57558439, compound

HRID 1723973Notes

Reaction equation

HRID 1723973 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:22])[C:20]=2[CH3:21])=[C:17]([OH:23])[CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.O.C(OCC)(=O)C>N1C=CC=CC=1>[C:1]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][S:10][C:11]2[O:12][C:13]3[C:18]([C:19](=[O:22])[C:20]=2[CH3:21])=[C:17]([O:23][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 57436857HCID 57436857, compound

Product 1

HCID 57558439HCID 57558439, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-tert-butylbenzylmercapto)-3-methyl-5-hydroxy chromen-4-one (5 g, 14.1 mmol) is dissolved in pyridine in a 25 mL round bottom flask and p-toluenesulfonyl chloride (15 mmol) is added to it. The reaction mixture is stirred for 8 hours. Water is then added to the flask and the contents are poured into a separatory funnel. Ethyl acetate is added and the layers are separated. The organic layer is then washed with water and brine and dried over sodium sulfate and filtered. The filtrate is concentrated in vacuo and the residue obtained is purified by silica gel flash chromatography (hexanes:ethyl acetate) to afford the above product.

Workup

  1. additionthe contents are poured into a separatory funnel
  2. customthe layers are separated
  3. washThe organic layer is then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue obtained
  8. customis purified by silica gel flash chromatography (hexanes:ethyl acetate)
  9. customto afford the above product

Sources & evidence

ORD record
ord-5373c29c56ca44958d3ab410ffc050f7
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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