Methyl 4-acetyl-4-tert-butoxycarbonyl-3-formyl-6-nonynoate → 5-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

HRID 46546ノート

反応式

HRID 46546 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

HCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 8082Piperidine溶媒

実験手順

A 790 mg quantity of the compound (7) 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 (2-a), R1 =t-Bu, R2 =CH3) in a yield of 78%, b.p. 82°-86° C./0.006 mm Hg.

後処理

  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

出典と根拠

ORDレコード
ord-312e7788dcf44f87908cc15390fccea2
出典データセット
uspto-grants-1979_11
特許番号
US04173707

反応ノート

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