Cesium carbonate → Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetate

HRID 865526Notes

Reaction equation

HRID 865526 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:20]([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[C:21]([O:23][CH3:24])=[O:22])=[C:3]([CH2:10][CH2:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 220112094-(Hydroxymethyl)-2-propylphenol

Product 1

HCID 19080423Methyl alpha-(4-hydroxymethyl-2-n-propyl-phenoxy)-3,4-methylenedioxyphenylacetateYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.84 g (23.13 mmol) of 4-hydroxy-3-n-propylbenzyl alcohol dissolved in 70 mL of anhydrous DMF was added 9.04 g (27.7 mmol) of cesium carbonate and the reaction mixture was magnetically stirred at room temperature for 15 minutes. Methyl α-bromo-3,4-methylenedioxyphenylacetate (7.58 g; 27.7 mmol) was added and the reaction mixture was then stirred for an additional 14 hours at room temperature under a nitrogen atmosphere. The reaction was then partitioned between 5% aqueous citric acid (700 mL) and EtOAc (100 mL) and extracted. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 40% EtOAc-hexane. The purified fractions were combined, evaporated, and dried in vacuo to afford 6.74 g (81%) of the title compound as a yellow oil.

Workup

  1. stirringthe reaction mixture was then stirred for an additional 14 hours at room temperature under a nitrogen atmosphere
  2. customThe reaction was then partitioned between 5% aqueous citric acid (700 mL) and EtOAc (100 mL)
  3. extractionextracted
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 40% EtOAc-hexane
  11. customevaporated
  12. customdried in vacuo

Sources & evidence

ORD record
ord-f66e4b0dbcdd4e3eac1278977119a308
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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