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

HRID 1287585Notes

Reaction equation

HRID 1287585 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 two 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-e3264698900446eca186aad4fe7504d4
Source dataset
uspto-grants-1976_10
Patent number
US03985733

Reaction notes

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