Sodium Hydroxide → 5-(1,3-dioxolan-2-yl)-2-oxo-pentanoic Acid

HRID 992201ノート

反応式

HRID 992201 の反応式
[OH-].[Na+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[CH2:8][CH2:9][CH2:10][C:11](=[O:17])[C:12]([O:14]CC)=[O:13].S(=O)(=O)(O)[O-].[K+]>CO>[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[CH2:8][CH2:9][CH2:10][C:11](=[O:17])[C:12]([OH:14])=[O:13]

参加物

5

反応物 3

HCID 14798Sodium Hydroxide2 回HCID 516920Potassium bisulfateHCID 22887850HCID 22887850、化合物2 回

生成物 1

HCID 98369745-(1,3-dioxolan-2-yl)-2-oxo-pentanoic Acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

A 3 L 3-necked round bottom flask was equipped with an overhead stirrer, thermocouple, and an addition funnel containing 1.5 N NaOH (460 mL). The flask was charged with MeOH (700 mL) and cooled to 0° C. The NaOH solution was added slowly to the methanol, maintaining the temperature below 10° C. and upon complete addition, the resulting solution was cooled to 0° C. A methanol solution of 5-(1,3-dioxolan-2-yl)-2-oxo-pentanoic acid, ethyl ester (350 mL) was added to the reaction via dropping funnel at a rate which maintained the temperature of the reaction mixture below 3° C. (addition time 1 hr). The reaction was stirred at 0° C. for 2 hours and the pH of the reaction was adjusted to 7.71 by the addition of 2 M potassium bisulfate (75 mL). The methanol was evaporated and the cloudy aqueous slurry was washed with MTBE (3×500 mL). The pH of the aqueous layer was adjusted to 4.5 by the addition of 2 M potassium bisulfate (100 mL) and extracted with ethyl acetate (500 mL). The pH of the aqueous layer was further adjusted to 2.0 by the addition of 2 M potassium bisulfate (50 mL), and extracted with ethyl acetate (2×500 mL). The combined ethyl acetate extracts were dried over magnesium sulfate and concentrated to afford 5-(1,3-dioxolan-2-yl)-2-oxo-pentanoic acid (60 g, 80 M % yield) as a thick liquid.

後処理

  1. customA 3 L 3-necked round bottom flask was equipped with an overhead stirrer
  2. temperaturemaintaining the temperature below 10° C.
  3. additionupon complete addition
  4. temperaturethe resulting solution was cooled to 0° C
  5. temperaturemaintained
  6. additionthe temperature of the reaction mixture below 3° C. (addition time 1 hr)
  7. customThe methanol was evaporated
  8. washthe cloudy aqueous slurry was washed with MTBE (3×500 mL)
  9. additionThe pH of the aqueous layer was adjusted to 4.5 by the addition of 2 M potassium bisulfate (100 mL)
  10. extractionextracted with ethyl acetate (500 mL)
  11. additionThe pH of the aqueous layer was further adjusted to 2.0 by the addition of 2 M potassium bisulfate (50 mL)
  12. extractionextracted with ethyl acetate (2×500 mL)
  13. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulfate
  14. concentrationconcentrated

出典と根拠

ORDレコード
ord-1092d12349fc49889bc2a075811a22cf
出典データセット
uspto-grants-2002_10
特許番号
US06468781B1

反応ノート

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