1,3-Cyclohexanedione → HCID 70421324, compound

HRID 247386Notes

Reaction equation

HRID 247386 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.O[N:10]=[C:11]1[CH2:15][CH2:14][CH2:13][C:12]1=O>C(O)(=O)C.[Zn]>[CH2:14]1[C:15]2[CH:11]([NH:10][CH:1]3[C:2]=2[C:3](=[O:7])[CH:4]=[CH:5][CH2:6]3)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 73664614HCID 73664614, compound

Product 1

HCID 70421324HCID 70421324, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 27.6 g (0.25 mole) of 1,3-cyclohexanedione and 27.6 g (0.244 mole) of the crude 2-hydroxyiminocyclopentanone in 435 mL of 70% aqueous acetic acid was added 47.6 g (0.73 g-atom) of zinc powder in about 5 g portions. The reaction was exothermic, but did not reach reflux. The mixture was heated to 80°-85° C. under argon for 2 hours and poured into 1.3 L of ice water and extracted with 3×300 mL of methylene chloride. The methylene chloride extracts were washed to neutrality with 3×500 mL of saturated sodium bicarbonate solution, dried over Na2SO4, and concentrated on a rotary evaporator to 50° C.

Workup

  1. temperaturedid not reach reflux
  2. temperatureThe mixture was heated to 80°-85° C. under argon for 2 hours
  3. extractionextracted with 3×300 mL of methylene chloride
  4. washThe methylene chloride extracts were washed to neutrality with 3×500 mL of saturated sodium bicarbonate solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated on a rotary evaporator to 50° C.

Sources & evidence

ORD record
ord-dbcff99fe5cd4308b2c87e732a0f068b
Source dataset
uspto-grants-1987_11
Patent number
US04707484

Reaction notes

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