Methyl 4-acetyl-4-methoxycarbonyl-3-formyl-6-nonynoate → HCID 20387587, compound

HRID 972101Notes

Reaction equation

HRID 972101 reaction equation
[C:1]([C:4]([C:18]([O:20][CH3:21])=[O:19])([CH2:13][C:14]#[C:15][CH2:16][CH3:17])[CH:5]([CH:11]=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH3:21][O:20][C:18]([C:4]1([CH2:13][C:14]#[C:15][CH2:16][CH3:17])[C:1](=[O:3])[CH:2]=[CH:11][CH:5]1[CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:19]

Participants

5

Reactant 1

HCID 20387588Methyl 4-acetyl-4-methoxycarbonyl-3-formyl-6-nonynoate

Product 1

HCID 20387587HCID 20387587, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 8082PiperidineSolvent

Procedure

The compound (3) (500 mg) obtained above is dissolved in 200 ml of benzene containing 1 ml of acetic acid and 1 ml of piperidine, and the solution is refluxed for 6 hours. On completion of the reaction, the solvent is removed and the residue dissolved in ethyl acetate. The solution is washed with 10% hydrochloric acid and an aqueous solution of sodium bicarbonate and then dried. The product is concentrated, and the residue purified by a silica gel column, giving 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (1-a), R1 =R2 =CH3) in a yield of 81%, b.p. 110°-115° C./0.15 mm Hg.

Workup

  1. temperaturethe solution is refluxed for 6 hours
  2. customOn completion of the reaction
  3. customthe solvent is removed
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe solution is washed with 10% hydrochloric acid
  6. dry with materialan aqueous solution of sodium bicarbonate and then dried
  7. concentrationThe product is concentrated
  8. customthe residue purified by a silica gel column

Sources & evidence

ORD record
ord-b03a208878eb4451bc81cacf90a92cc6
Source dataset
uspto-grants-1979_07
Patent number
US04163111

Reaction notes

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