Diethyl Malonate → Diethyl (3-methylbut-2-enyl)malonate

HRID 2372531

반응식

HRID 2372531 반응식
[H-].[Na+].CCCCC.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:19](Br)[CH:20]=[C:21]([CH3:23])[CH3:22]>O1CCCC1.CN(C)C=O>[CH3:22][C:21]([CH3:23])=[CH:20][CH2:19][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

7

반응물 4

HCID 7761Diethyl MalonateHCID 8003PentaneHCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-

생성물 1

HCID 89748Diethyl (3-methylbut-2-enyl)malonate수율 89.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

422 mg (14.1 mmol, 80% mineral oil dispersion) sodium hydride was washed 3 ×, each with 5 mL pentane, and suspended in a mixture of 10 mL tetrahydrofuran and 5 mL dimethylformamide. 2.04 g (13.4 mmol) diethyl malonate was added, and the mixture stirred for 40 mins to form a clear light brown solution. Prenyl bromide (2.00 g, 13.4 mmol) was then added, and the solution refluxed for 1 hr. The reaction was quenched with water, acidified to pH 2 with 1N HCl, and extracted 2 ×, each with 10 mL diethyl ether. The organic phases were dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane, furnished 2.734 g of a clear colorless oil in 12 mL fractions 4-16.

후처리

  1. customto form a clear light brown solution
  2. temperaturethe solution refluxed for 1 hr
  3. customThe reaction was quenched with water
  4. extractionextracted 2 ×
  5. dry with materialThe organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted with 50 mL each of 2%, 4%, 7%, 10%, and 15% diethyl ether/hexane

출처 및 근거

ORD 기록
ord-c833dd45b11b43389427f833305eb0d0
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05099020

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