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

HRID 1879091Notes

Reaction equation

HRID 1879091 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-cfc73570ae884f2e9622b3b3c82f47ce
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

Loading…