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

HRID 261632노트

반응식

HRID 261632 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 8082Piperidine용매

실험 절차

A 790 mg quantity of the compound (8) 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), R1 =t-Bu, R2 =CH3) is a yield of 78%, b.p. 82°-86° C./0.006 mm Hg.

후처리

  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

출처 및 근거

ORD 기록
ord-57e099f8cbf34cecbb2dd3390e15e86a
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166188

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