Water → 2-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

HRID 223784

反応式

HRID 223784 の反応式
[OH2:1].[CH3:2][C:3]1[O:7][C:6]([CH:8]([CH2:10][C:11]#[CH:12])O)=[CH:5][CH:4]=1.[OH-].[Na+].[Cl-].[Na+]>C([O-])(=O)C.[Na+].C(O)(=O)C>[CH2:10]([CH:8]1[C:3]([OH:7])([CH3:2])[CH:4]=[CH:5][C:6]1=[O:1])[C:11]#[CH:12]

参加物

7

反応物 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide2 回HCID 98774181-(5-Methylfuran-2-yl)but-3-yn-1-ol

生成物 1

HCID 130367862-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

試薬・触媒・溶媒 2

HCID 517045Sodium Acetate触媒HCID 176Acetic Acid溶媒

反応条件

温度
40 °C

実験手順

In a reaction vessel, water (1600 ml), anhydrous sodium acetate (0.4 g) and 5-methyl-2-furylpropargylcarbinol (20 g) were charged, and the temperature was elevated to reflux. The pH value was adjusted to 4.5 with an aqueous 0.5 N acetic acid solution, and the mixture was stirred under reflux for 13 hours while maintaining a pH value of 4.0 to 5.0 by the addition of an aqueous 1/3 N NaOH solution. Then, the reaction mixture was cooled to 40° C., neutralized with an aqueous 1/3 N NaOH solution and, after addition of sodium chloride (300 g), extracted with methyl isobutyl ketone (400 ml) five times. From the extract, methyl isobutyl ketone was removed by distillation at 60° c. under reduced pressure to give an oily substance (16 g), which was subjected to distillation under reduced pressure to obtain 2-propargyl-3-hydroxy-3-methyl-4-cyclopentenone (14.8 g). Yield, 74%. B.P., 115°-132° C./0.1 mmHg. nD25 1.5124. C13NMR spectrum (CDCl3, internal standard TMS, δ ppm, 22.6 MHz): 206.2 (1-C); 167.8 (5-C); 130.7 (4-C); 82.0 (--CH2 -C≡CH); 78.5 (3-C); 70.6 (--CH2 --C≡CH); 57.0 (2-C); 23.4 (--CH3); 14.7 (--CH2 --C≡CH).

後処理

  1. temperatureto reflux
  2. temperatureunder reflux for 13 hours
  3. temperaturewhile maintaining a pH value of 4.0 to 5.0
  4. extractionextracted with methyl isobutyl ketone (400 ml) five times
  5. customFrom the extract, methyl isobutyl ketone was removed by distillation at 60° c
  6. customunder reduced pressure to give an oily substance (16 g), which
  7. distillationwas subjected to distillation under reduced pressure

出典と根拠

ORDレコード
ord-e6226aaea418417284b4319816bfead6
出典データセット
uspto-grants-1982_10
特許番号
US04356326

関連ノート

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