Dimethylformamide → HCID 19934855, compound

HRID 37238Notes

Reaction equation

HRID 37238 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])[CH2:2][CH3:3].[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+].CN(C)[CH:24]=[O:25]>>[CH2:1]([C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[O:15][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][C:16]([O:25][CH3:24])=[O:19])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 10796Cesium carbonateHCID 190803892,6-Di-propyl-4-hydroxymethylphenol

Product 1

HCID 19934855HCID 19934855, compoundYield 35%

Procedure

To a solution of 1.014 g (4.87 mmol) of 2,6-di-propyl-4-hydroxymethylphenol dissolved in 10 mL of anhydrous dimethylformamide was added 2.379 g of cesium carbonate and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. A solution of methyl cx-bromo-phenylacetate dissolved in 2 mL DMF was added and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and partitioned between water and EtOAc. The organic layer was washed with brine, separated, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 20% EtOAc-hexane and combination of the purified fractions afforded 0.598 g (35%) of the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 60° C. overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between water and EtOAc
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residual oil was purified on a silica gel flash chromatography column
  11. washeluted with 20% EtOAc-hexane and combination of the purified fractions

Sources & evidence

ORD record
ord-7dacfb6e45e24513870bfc94a1a23e66
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

Loading…