p-Toluenesulfonic acid → HCID 20394599、化合物

HRID 261633ノート

反応式

HRID 261633 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 20394599HCID 20394599、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37c6b030506c405783bbd01c0af83635
出典データセット
uspto-grants-1979_08
特許番号
US04166188

反応ノート

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