Iodine → HCID 59692080, compound

HRID 898668Notes

Reaction equation

HRID 898668 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([CH3:15])([CH3:14])[CH2:8][C:7]2([CH3:17])[CH3:16])(=[O:3])[CH3:2].[I:18]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([I:18])[CH:13]=1)[O:10][C:9]([CH3:15])([CH3:14])[CH2:8][C:7]2([CH3:17])[CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 156611361-(2,2,4,4-Tetramethyl-3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one2×

Product 1

HCID 59692080HCID 59692080, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-acetyl-2,2,4,4-tetramethyl chroman (Compound 34, 0.36 g, 1.55 mmol) in anhydrous dichloromethane (5 mL) was treated with silver(I)trifluoromethanesulfonate (0.398 g, 1.55 mmol) and iodine (0.393 g, 1.55 mmol) and the resulting solution was stirred at ambient temperature for 4 h. The reaction mixture was treated with saturated, aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 4-10% ethyl acetate in hexane as the eluent to afford the title compound (0.47 g, 85%) as a viscous oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a residue which

Sources & evidence

ORD record
ord-45ee7288e2084c899580357585a5a821
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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