Cesium carbonate → HCID 28964239, compound

HRID 2060035Notes

Reaction equation

HRID 2060035 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chloride2×HCID 1425504-Hydroxy-3-nitrobenzyl alcohol

Product 1

HCID 28964239HCID 28964239, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(hydroxymethyl)-2-nitrophenol (2.20 g, 13.01 mmol) in DMF (60 mL) was added cesium carbonate (8.48 g, 26.0 mmol) followed by the portionwise addition of 4-methoxybenzyl chloride (3.06 g, 19.51 mmol). After stirring at rt for 45 mins additional 4-methoxybenzyl chloride (2.037 g, 13.01 mmol) was added followed by tetrabutylammonium iodide (2.402 g, 6.50 mmol). The reaction mixture was stirred at rt for 18 hr and then diluted with EtOAc (200 mL) and washed successively with water, 10% aq. K2CO3, water and finally brine, dried (MgSO4), filtered and concentrated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with 10-50% EtOAc in isohexane to afford the title compound as a cream solid, 2.17 g, 57.7%.

Workup

  1. additionwas added
  2. washwashed successively with water, 10% aq. K2CO3, water and finally brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 10-50% EtOAc in isohexane

Sources & evidence

ORD record
ord-bdf572e0a1fe4776b3992dd29ef9db93
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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