p-Toluenesulfonic acid → HCID 20394599, 화합물

HRID 261633노트

반응식

HRID 261633 반응식
C(OC([C:8]1([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH:8]([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10]1)=[O:16]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 203065655-Tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone

생성물 1

HCID 20394599HCID 20394599, 화합물

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A 800 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone is dissolved in 50 ml of benzene, and 30 mg of p-toluenesulfonic acid is added to the solution. The mixture is refluxed for 30 minutes. The resulting reaction mixture is neutralized with sodium bicarbonate, and the solvent removed. The residue is purified by a silica gel column and distilled in a vacuum, giving 4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (3), R2 =CH3) in a yield of 93%, b.p. 102°-103° C./3 mm Hg.

후처리

  1. temperatureThe mixture is refluxed for 30 minutes
  2. customThe resulting reaction mixture
  3. customthe solvent removed
  4. customThe residue is purified by a silica gel column
  5. distillationdistilled in a vacuum

출처 및 근거

ORD 기록
ord-37c6b030506c405783bbd01c0af83635
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166188

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