[Hydroxy(tosyloxy)iodo]benzene → HCID 86665799, compound

HRID 1623219Notes

Reaction equation

HRID 1623219 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][C:17]3=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.OI(C1C=CC=CC=1)OS(C1C=CC(C)=CC=1)(=O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH:19]=[CH:18][C:17]3=[O:24])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 325434[Hydroxy(tosyloxy)iodo]benzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 59318294HCID 59318294, compound

Product 1

HCID 86665799HCID 86665799, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound was produced with reference to the method described in the literature (Synth. Commun., 1994, 24 (18), 2637). A solution of 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (15.0 g, 43 mmol), [hydroxy(tosyloxy)iodo]benzene (20.4 g, 52 mmol) and p-toluenesulfonic acid monohydrate (375 mg) in acetonitrile (750 mL) was stirred at 50° C. for 16 hours. The solvent was distilled off under reduced pressure. Ethyl acetate (500 mL) was added to the obtained concentrated residue, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine in this order and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:2) to obtain the title compound (RE7) (4.92 g, 33%) as a pale yellow solid.

Workup

  1. customThe compound was produced with reference to the method
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionEthyl acetate (500 mL) was added to the obtained concentrated residue
  4. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→1:2)

Sources & evidence

ORD record
ord-4837e06c3b9e4d328c025232c50aee63
Source dataset
uspto-grants-2014_07
Patent number
US08778970B2

Reaction notes

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