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

HRID 1198045

반응식

HRID 1198045 반응식
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]

참가 물질

6

반응물 4

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 8166Dodecanoyl chloride2회HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-ca4d265a44794933be028d4e3fec5837
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278326

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