Tetrahydrofuran → 5-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanone

HRID 1605528Notes

Reaction equation

HRID 1605528 reaction equation
[Li].[CH3:2][C:3]1([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[O:7][CH2:6][CH2:5][O:4]1.O1CCC[CH2:15]1.C[Li]>C(OCC)C>[CH3:2][C:3]1([CH2:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:15])[O:4][CH2:5][CH2:6][O:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 13551185HCID 13551185, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 104196285-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

348 Mg. of the lithium salt of the ketal acid, 4-(2-methyl-1,3-dioxolan-2-yl)butanoic acid was dissolved in 5 ml. anhydrous tetrahydrofuran. The solution was cooled to 0° C and 1.25 ml. of a 1.6 molar solution of methyllithium in diethylether was added dropwise over a period of one hour while stirring under a nitrogen atmosphere. The solution was allowed to rise approximately to 20° C and kept at this temperature over a period of 2 hours. The reaction mixture was added to crushed ice and the organic solvents were removed in vacuo. The residue was extracted with ether, the extract was washed with a saturated sodium chloride solution, dried with magnesium sulfate, filtered and evaporated in vacuo to give crude 5-(2-methyl-1,3-dioxolan-2-yl)-2-pentanone.

Workup

  1. customto rise approximately to 20° C
  2. additionThe reaction mixture was added
  3. customto crushed ice
  4. customthe organic solvents were removed in vacuo
  5. extractionThe residue was extracted with ether
  6. washthe extract was washed with a saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-8a315ade16e54d6ab22cc5ad1e7e0e06
Source dataset
uspto-grants-1976_04
Patent number
US03950389

Reaction notes

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