1-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehyde → HCID 22042415, compound

HRID 1790880Notes

Reaction equation

HRID 1790880 reaction equation
[CH2:1]([Li])CCC.[CH3:6][C:7]1([C:12]2([CH:15]=O)[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9][O:8]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH:15]([C:12]1([C:7]2([CH3:6])[O:8][CH2:9][CH2:10][O:11]2)[CH2:13][CH2:14]1)=[CH2:1]

Participants

5

Reactant 2

HCID 143755571-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 22042415HCID 22042415, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

44.6 g of methyltriphenylphosphonium bromide in 700 ml of diethyl ether is introduced, and 50 ml of n-butyllithium solution (2.5 M in hexane) is added in drops at 0° C. under nitrogen. It is stirred for 1 more hour at room temperature and then 9.5 g of 7 in 10 ml of diethyl ether is added. After 1 hour, the reaction solution is quenched with sodium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 5.4 g of title compound 8 is obtained as a colorless oil.

Workup

  1. customthe reaction solution is quenched with sodium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium chloride solution
  4. customdried on sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-97f445886d124fe785ad845c9c6fd3fd
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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