Methyl vinyl ketone → [7-(1-Ethyl-propylidene)-bicyclo[2.2.1]hept-2-yl]ethanone

HRID 1828672노트

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HRID 1828672 반응식
[CH2:1]([C:3]([CH2:9][CH3:10])=[C:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[CH3:2].[CH3:11][C:12](C=C)=[O:13].[C:16]1(C)C=CC=C[CH:17]=1.CCCCCC>[Pd]>[CH2:1]([C:3](=[C:4]1[CH:8]2[CH2:16][CH2:17][CH:5]1[CH:6]([C:12](=[O:13])[CH3:11])[CH2:7]2)[CH2:9][CH3:10])[CH3:2]

참가 물질

5

반응물 3

HCID 6570Methyl vinyl ketoneHCID 112057726,6-Diethyl-fulveneHCID 21889329Toluene hexane

생성물 1

HCID 22057667[7-(1-Ethyl-propylidene)-bicyclo[2.2.1]hept-2-yl]ethanone수율 50%

시약·촉매·용매 1

HCID 23938Palladium촉매

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온도
50 °C

실험 절차

A mixture of 6,6-diethyl-fulvene (prepared as described in J. Org. Chem., 1990, 55, 3395; 86.0 g, 0.64 mol) and methyl-vinyl-ketone (44.9 g, 0.64 mol) was stirred for 5 h at 50° C. The mixture was cooled to room temperature and diluted with toluene/hexane (1/9, 600 ml). The solution was hydrogenated at normal pressure using palladium on charcoal (10%) as a catalyst. After 5 h the mixture was filtered, concentrated in vacuo and the residue was distilled (bp. 70° C./0.01 Torr) to yield the title compound (65.5 g, 50%) as a mixture of 2 isomers in a ratio of 3:1. Odor description: Woody, floral, Vertofix, Lilial, ambery.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationAfter 5 h the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. distillationthe residue was distilled (bp. 70° C./0.01 Torr)

출처 및 근거

ORD 기록
ord-624af58861444747ba054c44d5aff94f
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060664B2

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