Potassium Carbonate → HCID 69411429, compound

HRID 889845Notes

Reaction equation

HRID 889845 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36](=[O:39])[CH2:37]Br>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:37][C:36]([O:35][CH3:34])=[O:39])=[C:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 14852538HCID 14852538, compound

Product 1

HCID 69411429HCID 69411429, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

In DMF (15 mL) was stirred 4-hydroxy-1,3-benzenedicarboxylate dibenzyl ester (500 mg, 1.4 mmol) and potassium carbonate (276 mg, 2.0 mmol). To this was added methylbromoacetate (230 mg, 1.5 mmol) and the solution warmed to 50° C. and stirred 120 hours. The mixture filtered free of insoluble material and the DMF solution evaporated at reduced pressure to give a red oil. The oil was dissolved in ethyl acetate (50 mL) and washed successively with 10% citric acid (50 ML), saturated sodium bicarbonate solution (50 mL), and brine (50 mL). The organic phase dried over magnesium sulfate and evaporated at reduced pressure to give an oil. The oil was purified by MPLC (90 g silica gel, 2:1[hexane:ethyl acetate]) to give 330 mg (54%) of a clear oil. MS: M+1=435.2.

Workup

  1. filtrationThe mixture filtered free of insoluble material
  2. customthe DMF solution evaporated at reduced pressure
  3. customto give a red oil
  4. washwashed successively with 10% citric acid (50 ML), saturated sodium bicarbonate solution (50 mL), and brine (50 mL)
  5. dry with materialThe organic phase dried over magnesium sulfate
  6. customevaporated at reduced pressure
  7. customto give an oil
  8. customThe oil was purified by MPLC (90 g silica gel, 2:1[hexane:ethyl acetate])

Sources & evidence

ORD record
ord-4a46bc05838e4c5d82a3a7153384a0b5
Source dataset
uspto-grants-2006_02
Patent number
US06995151B2

Reaction notes

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