1,5-Diazabicyclo(4.3.0)non-5-ene → 1-(3-Butenyl)-1,4,5,6,7,8-Hexahydroanthraquinone

HRID 2420271노트

반응식

HRID 2420271 반응식
[C:1]1(=[O:12])[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:13]=[CH:14][CH:15]=[CH:16][CH2:17][CH2:18][CH:19]=[CH2:20].N12CCCC1=NCCC2>C(O)C.C1C=CC=CC=1>[CH2:17]([CH:16]1[C:2]2[C:1](=[O:12])[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[C:4](=[O:11])[C:3]=2[CH2:13][CH:14]=[CH:15]1)[CH2:18][CH:19]=[CH2:20]

참가 물질

6

반응물 3

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 101945Octa-1,3,7-trieneHCID 17958094Tetrahydronaphthoquinone

생성물 1

HCID 203114421-(3-Butenyl)-1,4,5,6,7,8-Hexahydroanthraquinone수율 49.1%

시약·촉매·용매 2

HCID 241Benzene용매HCID 702Ethanol용매2회

실험 절차

A mixture of 13.8 g of tetrahydronaphthoquinone (0.085 mole) and 10 g (0.092.5 mole) of 1,3,7-octatriene was refluxed for 11/2 hours in 100 ml of ethanol. After the addition of 1 ml of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), the mixture was stirred while exposed to air for 24 hours. The ethanol was then blown off and the residue was dissolved in benzene and chromatographed on acidic alumina. From the eluate, 11.2 g of crude product were obtained (49% yield). The crude product was rechromatographed on acidic alumina using a 3:1 mixture of cyclohexane/benzene as the eluent. After removal of the solvent, the product was recrystallized from methanol to yield an analytical product having a mp of 47° to 48° C.

후처리

  1. customchromatographed on acidic alumina

출처 및 근거

ORD 기록
ord-1d326b9677bf4c8f858f0ad88ec64d34
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04110353

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