Water → HCID 178525083, compound

HRID 2202252Notes

Reaction equation

HRID 2202252 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:15]1([C:22]([OH:24])=[O:23])[CH2:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16]1.O>CN(C=O)C>[C@H:15]1([C:22]([O:24][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:23])[CH2:18][C@@H:17]([C:19]([O:21][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:20])[CH2:16]1.[C@H:15]1([C:22]([O:24][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:23])[CH2:18][C@H:17]([C:19]([O:21][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:20])[CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 137582cis-Cyclobutane-1,3-dicarboxylic acid

Product 2

HCID 178525083HCID 178525083, compoundYield 23.6%HCID 178525084HCID 178525084, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (575 mg, 4.16 mmol) and benzyl bromide (0.495 mL, 4.16 mmol) were added to a solution of cyclobutane-1,3-dicarboxylic acid (cis-trans mixture) (200 mg, 1.39 mmol) in DMF (4.0 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0→5% ethyl acetate/hexane) to give dibenzyl cis-cyclobutane-1,3-dicarboxylate (106.3 mg, 0.328 mmol, 23.6%) as a less polar compound, and dibenzyl trans-cyclobutane-1,3-dicarboxylate (103.1 mg, 0.318 mmol, 22.9%) as a more polar compound, respectively. NMR spectrum of dibenzyl cis-cyclobutane-1,3-dicarboxylate

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 0→5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-57b17d7f91524ef0acd023bb917ea309
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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