2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 2-(benzofuran-3-yl)acetate

HRID 963221

Reaction equation

HRID 963221 reaction equation
[O:1]1[CH2:5][CH:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]1=2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[O:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]1=2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12171952130106-48-8

Product 1

HCID 7537531Ethyl 2-(benzofuran-3-yl)acetateYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution under N2 atmosphere containing ethyl 2,3-dihydrobenzo[b]furan-3-acetate (9.80 g, 47.6 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (12.97 g, 57.1 mmol) was heated at reflux for ~8 h. The reaction was filtered and the filtrate concentrated in vacuo. Silica gel chromatography (97:3 Hexane:EtOAc) of the residue afforded the title compound (7.24 g, 75%) as an orange oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for ~8 h
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8d11f425710f41199cde8cd1c36120dd
Source dataset
uspto-grants-1998_06
Patent number
US05763444

Linked notes

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