2-Methyl-1,3-cyclopentanedione → HCID 14897844, compound

HRID 1408947Notes

Reaction equation

HRID 1408947 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[B-](F)(F)(F)[F:10].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:10][C:2]1([CH3:1])[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8]

Participants

4

Reactant 2

HCID 130052-Methyl-1,3-cyclopentanedioneHCID 2724933Selectfluor

Product 1

HCID 14897844HCID 14897844, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methylcyclopentane-1,3-dione (4.50 g, 40.1 mmol) and Selectfluor (17.06 g, 48.2 mmol) in acetonitrile (80 mL) was heated to reflux for 2 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL), washed with saturated sodium bicarbonate, water, brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography, eluting with 20 to 50% ethyl acetate in hexanes, gave 2-fluoro-2-methylcyclopentane-1,3-dione (4.50 g, 82% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 2.65-3.19 (4H, m), 1.38-1.77 (3H, m).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate (200 mL)
  5. washwashed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography
  9. washeluting with 20 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c9caf95927dc40d5aaf2804e8e94faac
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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