Ethyl Bromide → 2-Ethyl-2-methacryloyloxyadamantane

HRID 1837324

反応式

HRID 1837324 の反応式
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[CH2:12](Br)[CH3:13].[Li].[C:16](Cl)(=[O:20])[C:17]([CH3:19])=[CH2:18].[OH-].[Na+]>O1CCCC1.CO>[C:16]([O:11][C:2]1([CH2:12][CH3:13])[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)(=[O:20])[C:17]([CH3:19])=[CH2:18]

参加物

8

反応物 5

HCID 6332Ethyl BromideHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 64151AdamantanoneHCID 3028194Lithium2 回

生成物 1

HCID 98136452-Ethyl-2-methacryloyloxyadamantane収率 29%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

15 g (0.1 mol) of 2-adamantanone obtained in Example 3 was dissolved in 50 ml of tetrahydrofuran, and 12 g (0.11 mol) of ethyl bromide was added to the resulting solution. 0.1 g of metal lithium was added to the solution each time until the total amount became 1.3 g (0.19 mol) in such a manner that the temperature of the solution should not exceed 30° C. while they were violently stirred. After the proceeding of a reaction was checked by gas chromatography and it was confirmed visually that the metal lithium disappeared, 10 g (0.1 mol) of methacrylic acid chloride was added to the reaction solution. After it was confirmed by gas chromatography that the reaction proceeded to the full, 3 ml of methanol and 3 ml of a 5% aqueous solution of sodium hydroxide were added to the reaction solution and stirred at room temperature for 1 hour to stop the reaction. Thereafter, the organic solvent was distilled off under reduced pressure, 200 ml of hexane was added, and the obtained solution was washed with a 10% aqueous solution of sodium hydroxide and 20% brine sequentially. Thereafter, hexane was distilled off under reduced pressure to obtain a crude product which was then recrystallized in isopropanol to obtain 7.2 g (0.029 mol, 29%) of 2-ethyl-2-adamantyl methacrylate.

後処理

  1. customexceed 30° C. while they
  2. additionwere added to the reaction solution
  3. stirringstirred at room temperature for 1 hour
  4. customthe reaction
  5. distillationThereafter, the organic solvent was distilled off under reduced pressure, 200 ml of hexane
  6. additionwas added
  7. washthe obtained solution was washed with a 10% aqueous solution of sodium hydroxide and 20% brine sequentially
  8. distillationThereafter, hexane was distilled off under reduced pressure
  9. customto obtain a crude product which
  10. customwas then recrystallized in isopropanol

出典と根拠

ORDレコード
ord-e0fb2af1278141949efe6a03f9c551a1
出典データセット
uspto-grants-2004_08
特許番号
US06781016B2

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