Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate → HCID 20306565, compound

HRID 1732433Notes

Reaction equation

HRID 1732433 reaction equation
[C:1]([C:4]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[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>[C: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])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 1

HCID 53669204Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate

Product 1

HCID 20306565HCID 20306565, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 8082PiperidineSolvent

Procedure

A 790 mg quantity of the compound (9) obtained above is dissolved in 50 ml of benzene containing 1 ml of acetic acid and 1 ml of piperidine, and the solution is refluxed for 4 hours. On completion of the reaction, the solvent is removed, and the residue dissolved in ethyl acetate. The solution is washed with water and an aqueous solution of sodium bicarbonate and thereafter dried. The residue is distilled in a vacuum, giving 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (10), R1 =t-Bu, R2 =CH3) in a yield of 78%, b.p. 82°-86° C./0.006 mm Hg.

Workup

  1. temperaturethe solution is refluxed for 4 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 water
  6. dry with materialan aqueous solution of sodium bicarbonate and thereafter dried
  7. distillationThe residue is distilled in a vacuum

Sources & evidence

ORD record
ord-13803dec78b64c6d835cc74c03f4fd61
Source dataset
uspto-grants-1980_12
Patent number
US04237308

Reaction notes

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