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

HRID 2420271ノート

反応式

HRID 2420271 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  1. customchromatographed on acidic alumina

出典と根拠

ORDレコード
ord-1d326b9677bf4c8f858f0ad88ec64d34
出典データセット
uspto-grants-1978_08
特許番号
US04110353

反応ノート

読み込み中…