2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57523622, compound

HRID 1468214Notes

Reaction equation

HRID 1468214 reaction equation
[CH3:1][C:2]1([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:7][CH:6]([C:8]#[N:9])[C:5](=[O:10])[CH2:4][CH2:3]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[CH3:1][C:2]1([C:11]#[C:12][Si:13]([CH3:15])([CH3:14])[CH3:16])[CH2:3][CH2:4][C:5](=[O:10])[C:6]([C:8]#[N:9])=[CH:7]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67114168HCID 67114168, compound

Product 1

HCID 57523622HCID 57523622, compoundYield 152.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5-methyl-2-oxo-5-((trimethylsilyl)ethynyl)cyclohexane-carbonitrile (270 mg) and DDQ (350 mg) in benzene (20 mL) was heated under reflux for 10 min. After removal of insoluble matter, the filtrate was concentrated in vacuo to give a residue (407 mg). The residue was purified by flash chromatography [hexanes-ethyl acetate (4:1)] to give 10 as a crystalline solid (142 mg, 78%): 1H NMR (acetone-d6) δ 7.71 (1H, d, J=1.5 Hz), 2.72 (1H, m), 2.62 (1H, m), 2.21 (2H, m), 1.55 (3H, s), 0.15 (9H, s); 13C NMR (acetone-d6) δ 192.0, 164.8, 116.4, 114.8, 106.5, 88.7, 35.9, 35.0, 0.0.

Workup

  1. temperatureunder reflux for 10 min
  2. customAfter removal of insoluble matter
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-92a358652c154c739c0d0d0726ef8d61
Source dataset
uspto-grants-2015_04
Patent number
US09000188B2

Reaction notes

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