Water → 4-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

HRID 1612996ノート

反応式

HRID 1612996 の反応式
[OH2:1].[OH-].[Na+].[OH:4][C:5]1[CH2:9][CH2:8][C:7](=O)[C:6]=1[CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>C(O)(=O)C>[OH:1][CH:8]1[CH2:9][C:5](=[O:4])[C:6]([CH2:11][CH2:12][C:13]#[C:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:7]1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 197774863-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

生成物 1

HCID 98595074-Hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone収率 76%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To the compound [VIII-1] (28.3 g, 0.12 mole) are added water (1200 g) and acetic acid (1.5 g), and the pH value thereof is adjusted to pH 4.4 with 5% aqueous sodium hydroxide solution. The mixture is heated with stirring at 100° C. for 25 hours. After completion of the reaction, the reaction mixture is cooled, extracted twice with methyl isobutyl ketone (300 ml) and separated. Methyl isobutyl ketone is distilled off from the organic layer to give a mixture (21.5 g, yield; 76%) of 4-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone (racemic 4-hydroxycyclopentenone) and 3-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone [IX-1] (ratio thereof=6:4).

後処理

  1. temperatureThe mixture is heated
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture is cooled
  4. extractionextracted twice with methyl isobutyl ketone (300 ml)
  5. customseparated
  6. distillationMethyl isobutyl ketone is distilled off from the organic layer

出典と根拠

ORDレコード
ord-26d38df399f24bbdb77d08fbb2a8e65f
出典データセット
uspto-grants-1993_03
特許番号
US05191109

反応ノート

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