Ethyl isobutyrate → 2,2-Dimethyl-3-oxo-tetradecanoic acid ethyl ester

HRID 1198045ノート

反応式

HRID 1198045 の反応式
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[Li]CCCC.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])C(C)C.[C:21](Cl)(=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CCOCC>[CH2:19]([O:18][C:13](=[O:17])[C:5]([CH3:6])([CH3:7])[C:21](=[O:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH3:20]

参加物

6

反応物 4

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 8166Dodecanoyl chloride2 回HCID 178418339Butyllithium

生成物 1

HCID 100632932,2-Dimethyl-3-oxo-tetradecanoic acid ethyl ester収率 98.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a cooled solution (-78° C.) of diisopropylamine (2.22 g, 0.022 mol) in 25 mL ether, n-BuLi (0.022 mol) was added dropwise and stirred for 20 minutes under a nitrogen atmosphere. Ethyl isobutyrate (2.65 g, 0.022 mol) was then added dropwise and the mixture was stirred for 20 minutes. In a separate flask, lauroyl chloride (5.0 g, 0.022 mol) was stirred in 10 mL ether and cooled to 0° C. The ethyl isobutyrate enolate solution was added dropwise to the lauroyl chloride solution over a 5-minute period. The reaction mixture was allowed to gradually warm to room temperature and stir for 16 hours (M. W. Rathke, et al, Tet. Lett., 2953 (1971)). The mixture was quenched with saturated ammonium chloride solution and extracted with ether two times. The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo (30° C.) to yield 6.5 g (0.021 mol, 98.9%) of the title compound.

後処理

  1. stirringthe mixture was stirred for 20 minutes
  2. temperatureto gradually warm to room temperature
  3. stirringstir for 16 hours (M. W. Rathke, et al, Tet. Lett., 2953 (1971))
  4. customThe mixture was quenched with saturated ammonium chloride solution
  5. extractionextracted with ether two times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo (30° C.)

出典と根拠

ORDレコード
ord-ca4d265a44794933be028d4e3fec5837
出典データセット
uspto-grants-1994_01
特許番号
US05278326

反応ノート

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