Coumarin → HCID 23054154, compound

HRID 2250985Notes

Reaction equation

HRID 2250985 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:15]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:16]1=[O:17].[F:26][C:27]([F:40])([F:39])[S:28]([O:31]S(C(F)(F)F)(=O)=O)(=[O:30])=[O:29]>ClCCl>[F:26][C:27]([F:40])([F:39])[S:28]([O-:31])(=[O:30])=[O:29].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:23]2[CH:24]=[C:25]3[C:20]([CH:19]=[CH:18][C:16](=[O:17])[O:15]3)=[CH:21][CH:22]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 323CoumarinHCID 13679Diphenyl sulfoxideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 23054154HCID 23054154, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 160 ml of dichloromethane were dissolved 20.2 g (0.1 mol) of diphenylsulfoxide and 17.5 g (0.12 mol) of coumarin, and 28.2 g (0.1 mol) of trifluoromethanesulfonic anhydride was added dropwise thereto at −70 to −60° C., followed by gradually warming to room temperature and reacting with stirring for 2 hours. After completion of the reaction, the obtained reaction solution was washed with water (160 ml×5 times) and concentrated under reduced pressure, followed by purifying the resulting crude product by a column chromatography to obtain 32.1 g of objective substance as pale yellow glassy substance (yield: 67%).

Workup

  1. additionwas added dropwise
  2. customat −70 to −60° C.
  3. customAfter completion of the reaction
  4. customthe obtained reaction solution
  5. washwas washed with water (160 ml×5 times)
  6. concentrationconcentrated under reduced pressure
  7. customby purifying the resulting crude product by a column chromatography
  8. customto obtain 32.1 g of objective substance as pale yellow glassy substance (yield: 67%)

Sources & evidence

ORD record
ord-a209878e9c9b4a2793379db6378c206d
Source dataset
uspto-grants-2008_01
Patent number
US07318991B2

Reaction notes

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