5-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanone → HCID 10975921, compound

HRID 1732263Notes

Reaction equation

HRID 1732263 reaction equation
[CH2:1]([Li])CCC.[CH2:6]1[CH2:17][O:16][C:8]([CH3:15])([CH2:9][CH2:10][CH2:11][C:12](=O)[CH3:13])[O:7]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:6]1[CH2:17][O:16][C:8]([CH3:15])([CH2:9][CH2:10][CH2:11][C:12]([CH3:1])=[CH2:13])[O:7]1

Participants

5

Reactant 2

HCID 104196285-(2-Methyl-1,3-dioxolan-2-yl)-2-pentanoneHCID 178418339Butyllithium2×

Product 1

HCID 10975921HCID 10975921, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of methyl triphenylphosphonium bromide (218 g) in anhydrous tetrahydrofuran (1.8 l) cooled to 0° C. is added 1.6 M n-butyllithium (270 ml) and 2.6 M n-butyllithium (37.5 ml). After stirring for 1 hour, 6,6-ethylenedioxy-heptane-2-one (91.3 g) in anhydrous tetrahydrofuran (200 ml) is added dropwise and the mixture stirred for 1.5 hours at room temperature. The reaction mixture is then filtered and the filter cake washed with ether. The solvent is removed via distillation at atmospheric pressure. The crude residue is purified via vacuum distillation to give 6,6-ethylenedioxy-2-methyl-hept-1-ene (33.95 g, 38%) bp 75°@15 mm:

Workup

  1. stirringthe mixture stirred for 1.5 hours at room temperature
  2. filtrationThe reaction mixture is then filtered
  3. washthe filter cake washed with ether
  4. customThe solvent is removed via distillation at atmospheric pressure
  5. distillationThe crude residue is purified via vacuum distillation

Sources & evidence

ORD record
ord-40bd4114b2f2412580ea9cfcef43d33b
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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