Methanol → HCID 14722453, compound

HRID 1031667Notes

Reaction equation

HRID 1031667 reaction equation
Br[CH:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH2:3]1.[CH3:25][OH:26]>F[B-](F)(F)F.[Ag+]>[CH3:25][O:26][CH:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 10621601HCID 10621601, compound

Product 1

HCID 14722453HCID 14722453, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Procedure

There were mixed 4.12 g of 3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one, 9.37 g of silver tetrafluoroborate and 100 ml of methanol. The mixture was refluxed for 4 hours. The reaction mixture was cooled and filtered to remove the insolubles. The filtrate was subjected to distillation under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluant: a 5 : 1 mixture of toluene and ethyl acetate) to obtain 1.27 g (yield: 35%) of 2,3-dihydro-3-methoxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto remove the insolubles
  5. distillationThe filtrate was subjected to distillation under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by a column chromatography (eluant
  8. additiona 5 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-3236888891234dd3bdc986e52efe8ff2
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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