Water → 2-(5-Oxiranyl-furan-2-yl)-[1,3]dioxolane

HRID 2080111Notes

Reaction equation

HRID 2080111 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1.[Br-].[CH3:14][S+](C)C.[OH-].[K+].O>C(#N)C>[O:12]1[CH2:14][CH:11]1[C:9]1[O:10][C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2735154Sulfonium, trimethyl-, bromide (1:1)HCID 146165975-(1,3-Dioxolan-2-yl)furan-2-carbaldehyde

Product 1

HCID 231307652-(5-Oxiranyl-furan-2-yl)-[1,3]dioxolaneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-[1,3]Dioxolan-2-yl-furan-2-carbaldehyde (2.03 g, 12.1 mmol), trimethylsulfonium bromide (1.90 g, 12.1 mmol) and potassium hydroxide (779 mg, 13.9 mmol) were suspended in acetonitrile (75 mL), and the solution was stirred overnight at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, 2-(5-oxiranyl-furan-2-yl)-[1,3]dioxolane (2.25 g) was obtained as a pale yellow oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f386fb9bc7834aaca3b002b00c2987de
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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