Cesium carbonate → HCID 90387289, compound

HRID 1468594Notes

Reaction equation

HRID 1468594 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+].Br[CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31]>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][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])=[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 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 90387289HCID 90387289, compoundYield 87%

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-bromo-2-(2-methoxyethoxy)ethane (9 mmol) was 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 provide pure 1-methoxy-4-[2-(2-methoxyethoxy)ethoxy]-2,5-di-tert-butyl-benzene in an 87% yield. 1H NMR (300 MHz, CDCl3): δ/ppm 6.83 (s, 1H), 6.82 (s, 1H), 4.14 (t, J=4.5 Hz, 2H), 3.89 (t, J=4.5 Hz, 2H), 3.80 (s, 3H), 3.72 (t, J=4.5 Hz, 2H), 3.58 (t, J=4.5 Hz, 2H), 3.40 (s, 3H), 1.38 (s, 9H)), and 1.35 (s, 9H). The purity was over 99.5% based GC-mass spectroscopy, and the molecular weight was observed at 338.3, which is consistent with the theoretical value, 338.5.

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-adf58b4dd7c5471ba9ef27d4d5b1a060
Source dataset
uspto-grants-2015_04
Patent number
US09005822B2

Reaction notes

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