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2-Methyl-3-butyn-2-ol → 2-(1,1-Dimethylprop-2-ynyloxy)propionic acid methyl ester

HRID 341648
ノート
印刷プレビュー

反応式

HRID 341648 の反応式
[H-].[Na+].[CH3:3][C:4]([OH:8])([C:6]#[CH:7])[CH3:5].[CH3:9][O:10][C:11](=[O:15])[CH:12](Br)[CH3:13]>O1CCCC1>[CH3:9][O:10][C:11](=[O:15])[CH:12]([O:8][C:4]([CH3:5])([CH3:3])[C:6]#[CH:7])[CH3:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 82582-Methyl-3-butyn-2-olHCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionate

生成物 1

HCID 595626712-(1,1-Dimethylprop-2-ynyloxy)propionic acid methyl ester収率 88.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a mixture of sodium hydride (23.8 g, 0.595 mol) in tetrahydrofuran (400 ml) cooled to 0° C., is added a solution of 2-methyl-3-butyne-2-ol (50 g, 0.595 mol) in tetrahydrofuran (50 ml). The reaction mixture is stirred at 0° C. for 1 hour. A solution of methyl-2-bromo-propionate (99.36 g, 0.595 mol) in tetrahydrofuran (100 ml) is added to the reaction mixture slowly at 0° C. The reaction mixture is stirred at 0° C. for 2 hours and allowed to come to ambient temperature and stirred for 1 hour. The reaction mixture is cooled to 10° C. and quenched with ice cold water. The mixture is extracted with diethyl ether (3×200 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 2-(1,1-dimethylprop-2-ynyloxy)propionic acid methyl ester (90 g) as a colorless oil, used without further purification in the next step.

後処理

  1. stirringThe reaction mixture is stirred at 0° C. for 2 hours
  2. customto come to ambient temperature
  3. stirringstirred for 1 hour
  4. temperatureThe reaction mixture is cooled to 10° C.
  5. customquenched with ice cold water
  6. extractionThe mixture is extracted with diethyl ether (3×200 ml)
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe mixture is filtered
  10. customthe filtrate is evaporated under reduced pressure

出典と根拠

ORDレコード
ord-69b879a4537944f3951ba5106af4078f
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895761B2

反応ノート

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