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

HRID 972103Notes

Reaction equation

HRID 972103 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 (3) 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 (1-a), 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-00c3a069964e45d799f8b2682a41d998
Source dataset
uspto-grants-1979_07
Patent number
US04163111

Reaction notes

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