Cesium carbonate → HCID 57456868, compound

HRID 658245Notes

Reaction equation

HRID 658245 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH2:13][O:14][CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH2:24][O:25][CH3:26]>CN(C=O)C.CCOCC>[CH3:26][O:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH2:13][O:14][CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 57456867HCID 57456867, compound

Product 1

HCID 57456868HCID 57456868, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-hydroxy-5-(2-methoxyethyl)benzoate (1 eq.) from the previous step in DMF (0.2 M) was added Cs2CO3 (2 eq.) and 1-bromo-2-methoxy-ethane (2 eq.). The reaction was heated to 80° C. and stirred for 18 h. After cooling to rt, the reaction was diluted with ether and washed extensively with water and brine. The organic extract was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex) to afford the title compound as an oil.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed extensively with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex)

Sources & evidence

ORD record
ord-5d6852a09574417fa63d01e4469516a2
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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