2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(Benzofuran-5-yl)propan-1-one

HRID 626247Notes

Reaction equation

HRID 626247 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 40673881-(2,3-Dihydro-1-benzofuran-5-yl)propan-1-one

Product 1

HCID 673362701-(Benzofuran-5-yl)propan-1-oneYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(2,3-dihydrobenzofuran-5-yl)propan-1-one (40 g, 1.0 eq) and 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (62 g, 1.2 eq) in 400 mL anhydrous 1,4-dioxane was refluxed overnight, cooled, quenched with sat NaHCO3 (aq), and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography to give the desired product (10.3 g, 26%). 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=2.0 Hz, 1H), 7.98 (dd, J=8.8 Hz, 2.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.0 Hz, 1H), 3.07 (q, J=7.2 Hz, 2H), 1.26 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturecooled
  2. customquenched with sat NaHCO3 (aq)
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-1b1739f21da34daaa871147e73228e51
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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