Water → 1-Allyl 7-ethyl 2-allyloxycarbonyl-2-(4-cyanobenzyl)heptanedioate

HRID 1672692노트

반응식

HRID 1672692 반응식
[H-].[Na+].[CH2:3]([O:6][C:7]([CH:9]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[O:8])[CH:4]=[CH2:5].Br[CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1.O>CN(C)C=O>[CH2:3]([O:6][C:7]([C:9]([CH2:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[O:8])[CH:4]=[CH2:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 578313641-Allyl 7-ethyl 2-allyloxycarbonylheptanedioate

생성물 1

HCID 578313451-Allyl 7-ethyl 2-allyloxycarbonyl-2-(4-cyanobenzyl)heptanedioate수율 73.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

1.69 g (70.43 mmol) of sodium hydride are added in portions to a solution of 20 g (64.03 mmol) of 1-allyl 7-ethyl 2-allyloxycarbonylheptanedioate from Example 82A in 140 ml of dimethylformamide at 0° C. The reaction mixture is then allowed to reach room temperature and is stirred for 30 min. The reaction solution is cooled to 0° C. again and, after addition of 16.32 g (83.24 mmol) of 4-bromomethylbenzonitrile in 140 ml of DMF, stirred at this temperature for 30 min. The mixture is then stirred at room temperature overnight. Water is added dropwise to the reaction mixture and, after extraction three times with ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness in vacuo. The resulting crude product is purified by flash chromatography an silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1). 20.08 g (46.97 mmol, 73% yield) of a colorless solid are obtained.

후처리

  1. customto reach room temperature
  2. stirringstirred at this temperature for 30 min
  3. stirringThe mixture is then stirred at room temperature overnight
  4. extractionafter extraction three times with ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solvent is concentrated to dryness in vacuo
  9. customThe resulting crude product is purified by flash chromatography an silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1→1:1)

출처 및 근거

ORD 기록
ord-e3d7560f89ea4c80a678b6317bff781f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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