Water → HCID 23130349, compound

HRID 2080100Notes

Reaction equation

HRID 2080100 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[O:10][C:9]([CH:11]2OCC[O:12]2)=[CH:8][CH:7]=1.O1CCOC1C1OC=CC=1.C(O)(=O)C(O)=O.O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[O:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 2631582-Furyl-1,3-dioxolaneHCID 231303692-(5-(3-Fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane

Product 1

HCID 23130349HCID 23130349, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of a mixture of 2-(5-(3-fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane and 2-(1,3-dioxolan-2-yl)furan (8033 mg) in methanol (80 mL) was added an aqueous solution of oxalic acid (22 g, 115 mmol) (80 mL), and the solution was stirred at room temperature for 1 hour. Water was added to the reaction mixture, which extracted with diethyl ether, the organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (4084 mg, 20.0 mmol, 34%) was obtained.

Workup

  1. extractionextracted with diethyl ether
  2. washthe organic layer was sequentially washed with an aqueous solution of saturated sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d41305d67c344d098aa5758ef51c6d7c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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