Cesium carbonate → HCID 90386879, compound

HRID 1468593Notes

Reaction equation

HRID 1468593 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:24][O:25][CH:26](Br)[CH3:27]>CN(C)C=O>[CH3:12][O:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([O:17][CH2:27][CH2:26][O:25][CH3:24])=[CH:7][C:8]=1[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 748122,5-Di-tert-butyl-4-hydroxyanisoleHCID 218917521-Bromo-1-methoxyethane

Product 1

HCID 90386879HCID 90386879, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-di-tert-butyl-4-methoxyphenol (9 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 ml). Cesium carbonate (13 mmol) and 1-bromoethyl methyl ether (9 mmol) were added to the solution. The reaction mixture was then stirred at room temperature overnight. After removal of the solvent, the residue was partitioned between dichloromethane (DCM) and aqueous NaHCO3 (0.1 M). The organic portion was separated and dried over Na2SO4 and then the solvent was removed under vacuum. The crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1) to afford pure 1-methoxy-4-(2-methoxyethoxy)-2,5-di-tert-butyl-benzene in an 85% yield. 1H NMR (300 MHz, CDCl3): δ/ppm 6.84 (s, 1H), 6.83 (s, 1H), 4.11 (t, J=4.5 Hz, 2H), 3.78 (m, 5H), 3.45 (s, 3H), 1.38 (s, 9H), and 1.35 (s, 9H).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was partitioned between dichloromethane (DCM) and aqueous NaHCO3 (0.1 M)
  3. customThe organic portion was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed under vacuum
  6. customThe crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1)

Sources & evidence

ORD record
ord-d1eefa23fac44e48aff7aea2e0e387f6
Source dataset
uspto-grants-2015_04
Patent number
US09005822B2

Reaction notes

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