2,4,6-Trimethylphenol → HCID 21912175, compound

HRID 968003Notes

Reaction equation

HRID 968003 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=[C:4]([CH3:17])[N:3]=1.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27].CC(C)([O-])C.[K+]>C1COCC1>[CH2:13]([CH:12]([O:11][C:6]1[CH:5]=[C:4]([CH3:17])[N:3]=[C:2]([O:27][C:20]2[C:21]([CH3:26])=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=2[CH3:18])[C:7]=1[N+:8]([O-:10])=[O:9])[CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 21912196HCID 21912196, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21912175HCID 21912175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloro-4-(1-ethyl-propoxy)-6-methyl-3-nitro-pyridin (500 mg, 1.93 mmol), and 2,4,6-trimethylphenol (289 mg, 2.13 mmol) in dry THF was added potassium t-butoxide. The resulting mixture was stirred at rt. overnight. The mixture was quenched with water, brine and extracted 3 times with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness. After silica gel column chromatography purification, the title compound was obtained as a light yellow crystal, mp 106-109° C. Anal. For C20H26N2O4 calc. C, 67.02; H, 7.31; N, 7.82; found, C, 67.34; H, 7.40; N, 7.42.

Workup

  1. customovernight
  2. customThe mixture was quenched with water, brine
  3. extractionextracted 3 times with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness
  7. customAfter silica gel column chromatography purification

Sources & evidence

ORD record
ord-2a29341bd81940da977769a5f96f13ba
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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