Chloromethyl Methyl Ether → HCID 58047211, compound

HRID 1888719Notes

Reaction equation

HRID 1888719 reaction equation
[OH:1][C:2]1[CH:11]=[C:10](I)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH3:30][O:31][CH2:32]Cl>C(N(CC)CC)C.C(OCC)(=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:10]2[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:1][CH2:30][O:31][CH3:32])[CH:11]=2)=[CH:18][CH:17]=1)[CH3:14]

Participants

10

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 27751241-Ethoxy-4-ethynylbenzeneHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 58047211HCID 58047211, compoundYield 51%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-hydroxy-4-iodobenzoate (1.00 g, 3.60 mmol) and 1-ethoxy-4-ethynylbenzene (789 mg, 5.40 mmol) and copper(I) iodide (68.6 mg, 0.360 mmol) in triethylamine (9 mL) was added bis(triphenylphosphine)palladium(II) chloride (253 mg, 0.360 mmol), and the mixture was stirred under an argon stream at room temperature for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in DMF (10 mL). Potassium carbonate (2.59 g, 18.8 mmol) and chloromethyl methyl ether (1.07 mL, 14.0 mmol) were added thereto, and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to give the title compound (623 mg, yield 51%) as a yellow solid.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe obtained residue was dissolved in DMF (10 mL)
  5. stirringthe mixture was stirred at room temperature for 20 min
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed twice with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-2e46032c90004e4ea5dcf9952ab32e5e
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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