Cesium carbonate → HCID 66619457, compound

HRID 1242438Notes

Reaction equation

HRID 1242438 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[CH:5][C:3]=1[OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH4+].[Cl-]>CN(C=O)C>[CH2:22]([O:21][C:19](=[O:20])[C:18]([O:4][C:3]1[CH:5]=[CH:6][C:7]([OH:10])=[C:8]([CH3:9])[C:2]=1[CH3:1])([CH3:25])[CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 25517Ammonium ChlorideHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 66619457HCID 66619457, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 8.0 g (57.9 mmol) 2,3-dimethylhydroquinone and 39.6 g (121.6 mmol) cesium carbonate in 100 ml DMF was treated with 9.45 ml (63.7 mmol) of ethyl 2-bromo-2-methylpropionate and stirred for 2 days at RT. The reaction was poured on a mixture of saturated NH4Cl-solution and ice and extracted with AcOEt (3×). The organic phase was washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1, to give 5.4 g of the title compound as dark brown oil.

Workup

  1. extractionextracted with AcOEt (3×)
  2. washThe organic phase was washed with aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1

Sources & evidence

ORD record
ord-6548de9caff24a82ae64a375ce47055a
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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