Sodium Acetate → 1-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehyde

HRID 842621Notes

Reaction equation

HRID 842621 reaction equation
[CH3:1][C:2]1([C:7]2([CH2:10][OH:11])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4][O:3]1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH3:1][C:2]1([C:7]2([CH:10]=[O:11])[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 22042312[1-(2-Methyl-1,3-dioxolan-2-yl)cyclopropyl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 143755571-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehydeYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

10 g of 96 in 500 ml of methylene chloride is dissolved, and 3.7 g of sodium acetate (anhydrous) and 19.3 g of pyridinium chlorochromate are added. It is now stirred for 2 hours under argon. It is diluted with 1 l of diethyl ether and then filtered on Celite. Concentration by evaporation of the solvent followed by chromatographic purification on silica gel with ethyl acetate/hexane yields 8.1 g of 1-(2-methyl-1,3-dioxolan-2-yl)cyclopropanecarbaldehyde 97 as a colorless oil.

Workup

  1. filtrationfiltered on Celite
  2. concentrationConcentration
  3. customby evaporation of the solvent
  4. customfollowed by chromatographic purification on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-66deba23525644cf98e17f3e59f306a1
Source dataset
uspto-grants-2002_04
Patent number
US06376480B1

Reaction notes

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