Hydrochloric Acid → Ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropane carboxylate

HRID 236454

반응식

HRID 236454 반응식
[H-].[Na+].[I-].C[S+](C)(C)=O.[Br-].[C:10]([CH2:15][S+](C)C)([O:12][CH2:13][CH3:14])=[O:11].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][C:33]([C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][O:43][C:37]=3[CH:36]=2)=[O:34])[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28].Cl>CS(C)=O>[CH2:13]([O:12][C:10]([CH:15]1[CH:31]([C:23]2[CH:22]=[C:21]([O:20][CH3:19])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=2)[CH:32]1[C:33](=[O:34])[C:35]1[CH:40]=[CH:39][C:38]2[O:41][CH2:42][O:43][C:37]=2[CH:36]=1)=[O:11])[CH3:14]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 78861(2-Ethoxy-2-oxoethyl)dimethylsulphonium bromideHCID 47753113,4,5-Trimethoxy-3',4'-methylenedioxy chalcone

생성물 1

HCID 11059036Ethyl 2-(3,4-methylenedioxybenzoyl)-3-(3,4,5-trimethoxyphenyl)-cyclopropane carboxylate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

실험 절차

In a three-neck one-liter round-bottom flask, equipped with a magnetic stirrer, dropping funnel, nitrogen inlet and a septum was placed sodium hydride (8.2 g, 0.17 moles, 50% dispersion). The dispersion was washed with petroleum either (2×100 ml) and dried under nitrogen. Trimethylsulfoxonium iodide (37.7 g, 0.17 moles) was added, followed by a dropwise addition of dry dimethylsulfoxide (45 ml) via a syringe over a 30-minute period. The suspension was stirred at room temperature for 1.5 hours, and then a solution of carbethoxymethyl dimethylsulfonium bromide (41.2 g, 0.18 moles) in dimethylsulfoxide (60 ml) was added over a 10-minute period, under continuous stirring. The milky white suspension was further stirred at room temperature for 1.5 hours. A suspension of 3,4,5-trimethoxy-3',4'-methylenedioxy chalcone XXIIa (55.9 g, 0.16 moles) [prepared according to the procedure described by S. Wattanasin and W. S. Murphy, Synthesis, 647 (1980)] in dimethylsulfoxide (185 ml) was added in a steady stream over a 5-minute period, and then the reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was poured into cold 0.1N HCl (700 ml), and the resulting gummy material was separated from the aqueous solution. The aqueous solution was extracted from ether (2×500 ml). The combined extract together with an additional amount of ether (500 ml) was employed to dissolve the gummy precipitate. The etheral solution was sequentially washed with aqueous NaHCO3 solution (500 ml, 5%) and water, dried (Na2SO4 and MgSO4) and concentrated to yield the α-isomer of the title compound (68.0 g) as a light-yellow glass. The 1H NMR spectral data of this material was identical to the α-isomer reported by W. S. Murphy and S. Wattanasin, J.C.S. Perkin I, 271 (1982).

후처리

  1. customIn a three-neck one-liter round-bottom flask, equipped with a magnetic stirrer
  2. washThe dispersion was washed with petroleum either (2×100 ml)
  3. customdried under nitrogen
  4. stirringThe milky white suspension was further stirred at room temperature for 1.5 hours
  5. customprepared
  6. additionwas added in a steady stream over a 5-minute period
  7. stirringthe reaction mixture was stirred at room temperature for 17 hours
  8. customthe resulting gummy material was separated from the aqueous solution
  9. extractionThe aqueous solution was extracted from ether (2×500 ml)
  10. extractionThe combined extract together with an additional amount of ether (500 ml)
  11. dissolutionto dissolve the gummy precipitate
  12. washThe etheral solution was sequentially washed with aqueous NaHCO3 solution (500 ml, 5%) and water
  13. dry with materialdried (Na2SO4 and MgSO4)
  14. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8a82a44754fc4cdd95ba7ae3371ef675
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644072

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