Sodium hydride → Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonate

HRID 2187048노트

반응식

HRID 2187048 반응식
[H-].[Na+].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)[CH3:4].Br[CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26]>O1CCCC1>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]([CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5373944Ethyl (E)-4-bromobut-2-enoateHCID 133398183-Descarboxy Imazethapyr

생성물 1

HCID 22450183Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-crotonate수율 25.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A stirred suspension of sodium hydride (1.6 g, 53 mmol, 80% oil dispersion) in dry tetrahydrofuran is treated with a solution of 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline (10.24 g, 41.80 mmol) in dry tetrahydrofuran dropwise via addition funnel. After addition is complete and effervescence subsides, ethyl 4-bromocrotonate (12.9 g, 50.1 mmol, 75% technical grade) is added to the reaction mixture at once. The resulting mixture is stirred at room temperature under nitrogen for 19 hours. After this period, the reaction mixture is partitioned between water and ether. The layers are separated, and the organic layer is dried over magnesium sulfate, decolorized with activated charcoal, vacuum filtered through diatomaceous earth, and concentrated in vacuo to obtain a dark brown oil. The oil is purified by flash chromatography (2:1 hexanes/ethyl acetate eluent) to give the title product as a pale orange oil (3.78 g, 25%).

후처리

  1. additionAfter addition
  2. waitAfter this period
  3. customthe reaction mixture is partitioned between water and ether
  4. customThe layers are separated
  5. dry with materialthe organic layer is dried over magnesium sulfate
  6. filtrationfiltered through diatomaceous earth
  7. concentrationconcentrated in vacuo
  8. customto obtain a dark brown oil
  9. customThe oil is purified by flash chromatography (2:1 hexanes/ethyl acetate eluent)

출처 및 근거

ORD 기록
ord-00776f4f09514951b983d203bb3175d7
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06407217B1

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