HCID 24978441, compound → Ethyl γ-oxo-2-furanhexanoate

HRID 1484392Notes

Reaction equation

HRID 1484392 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8](=[O:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[H][H]>[Pd].C(#N)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8](=[O:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 24978441HCID 24978441, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89443100Ethyl γ-oxo-2-furanhexanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask was placed 1.334 g (6.000 mmol) of (E)-ethyl 6-(furan-2-yl)-4-oxohex-5-enoate. 6 mL of acetonitrile was added and stirring was begun. To this was added 0.064 g Pd/C (en) and hydrogen was added using a balloon (˜1 atm). The reaction mixture was stirred for 48 h and the mixture was then purified by flash column chromatography using 15% ether/hexane, v/v. Purification gave rise to 0.4817 g (73%) of the saturated system 1H (CDCl3) δ 1.25 (t, J=7 Hz, 3H), 2.6 (m, 2H), 2.8 (m, 2H), 2.9 (m, 2H), 3.0 (m, 2H), 4.16 (q, J=7 Hz), 6.0 (1H), 6.3 (1H), 7.3 (1H).

Workup

  1. customIn a round bottom flask was placed
  2. additionwas added
  3. stirringThe reaction mixture was stirred for 48 h
  4. customthe mixture was then purified by flash column chromatography
  5. customPurification
  6. customgave rise to 0.4817 g (73%) of the saturated system 1H (CDCl3) δ 1.25 (t, J=7 Hz, 3H), 2.6 (m, 2H), 2.8 (m, 2H), 2.9 (m, 2H), 3.0 (m, 2H), 4.16 (q, J=7 Hz), 6.0 (1H), 6.3 (1H), 7.3 (1H)

Sources & evidence

ORD record
ord-93ad75ab41774164a7560eb3ab250ec9
Source dataset
uspto-grants-2016_08
Patent number
US09422207B2

Reaction notes

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