Ethyl Acetate → HCID 58047427, compound

HRID 1888714Notes

Reaction equation

HRID 1888714 reaction equation
O[CH:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)[CH3:3].P([N:33]=[N+:34]=[N-:35])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[N:33]([CH:2]([C:4]1[O:5][C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:7]=2[CH:8]=1)[CH3:3])=[N+:34]=[N-:35]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 22481692HCID 22481692, compound

Product 1

HCID 58047427HCID 58047427, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 2-(1-hydroxyethyl)-1-benzofuran-6-carboxylate (1.10 g, 4.99 mmol) in toluene (20 mL) were added diphenyl azidophosphate (1.62 mL, 7.50 mmol) and DBU (1.50 mL, 9.98 mmol), and the mixture was stirred at room temperature for 2.5 hr. Ethyl acetate was added thereto, 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 purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 2:3) to give the title compound (1.22 g, yield 88%) as an oil.

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. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 2:3)

Sources & evidence

ORD record
ord-6c988b22b153412db8cb5047933afeae
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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