2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl benzofuran-7-carboxylate

HRID 380508Notes

Reaction equation

HRID 380508 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1.CCOCC>[C:1]([C:5]1[C:13]2[O:12][CH:11]=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15062252Methyl 2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 14229730Methyl benzofuran-7-carboxylateYield 116.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.31 g (1.22 mmol) of 7-Carbomethoxy dihydrobenzofuran and 1.66 g (3.3 mmol) of DDQ in 25 mL of toluene was heated at reflux for 7 h. The reaction mixture was then cooled to rt, diluted with ether, and washed with 3×30 mL of sat'd NaHCO3 solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1) to give 0.25 g of the title compound.

Workup

  1. temperatureat reflux for 7 h
  2. washwashed with 3×30 mL of sat'd NaHCO3 solution
  3. dry with materialThe organic fraction was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-727081f31fe44a289d8d73bd95a6e82c
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

Loading…