Iodo benzene diacetate → HCID 86673382, compound

HRID 1023344Notes

Reaction equation

HRID 1023344 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][OH:19])[CH:14]=3)[N:9]=2)=[CH:5][CH:4]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH:18]=[O:19])[CH:14]=3)[N:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 67327185HCID 67327185, compound

Product 1

HCID 86673382HCID 86673382, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (38 mL) solution of [2-(4-methoxyphenoxy)quinolin-6-yl]methanol (1.11 g) and iodobenzene diacetate (1.33 g) was added 2,2,6,6-tetramethyl-1-piperidinyloxy radical (61.0 mg), then the resultant mixture was stirred over night at room temperature. The reaction mixture was quenched by addition of saturated aqueous Na2S2O3 and NaHCO3, and extracted with CH2Cl2. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1 to 5/1) to afford 2-(4-methoxyphenoxy)quinoline-6-carbaldehyde (1.08 g) as a colorless solid.

Workup

  1. customThe reaction mixture was quenched by addition of saturated aqueous Na2S2O3 and NaHCO3
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1 to 5/1)

Sources & evidence

ORD record
ord-46657cb8999a43f59f99696d15d2b1c4
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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