Trimethylhydroquinone → 3,5,6-Trimethyl-2-[1-(3-pyridyl)ethyl]-1,4-benzoquinone

HRID 1030587

반응식

HRID 1030587 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7](O)[CH3:8])[CH:2]=1.[CH3:10][C:11]1[C:17]([CH3:18])=[C:16]([OH:19])[C:15]([CH3:20])=[CH:14][C:12]=1[OH:13].FC(F)(F)S(O)(=O)=O>ClC(Cl)C>[CH3:20][C:15]1[C:16](=[O:19])[C:17]([CH3:18])=[C:11]([CH3:10])[C:12](=[O:13])[C:14]=1[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:8]

참가 물질

5

반응물 3

HCID 12785TrimethylhydroquinoneHCID 62406Trifluoromethanesulfonic acidHCID 101192alpha-Methyl-3-pyridinemethanol

생성물 1

HCID 142777653,5,6-Trimethyl-2-[1-(3-pyridyl)ethyl]-1,4-benzoquinone수율 61.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 4.0 g (32.5 mmol) of 1-(3-pyridyl)ethanol in 25 ml of dichloroethane, 4.96 g (32.6 mmol) of 2,3,5-trimethylhydroquinone and 4.5 ml (50.9 mmol) of trifluoromethanesulfonic acid were added and refluxed by heating for 20 hours in argon atomosphere. After cooling, ice water was added, washed with ethyl acetate to eliminate neutral substances, and made weakly alkaline with a saturated solution of sodium hydrogen carbonate. The resultant substance was extracted with ethyl acetate, and the extract was washed with water, dried, oxidized with air and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:2)), to give 5.1 g of 3,5,6-trimethyl-2-[1-(3-pyridyl)ethyl]-1,4benzoquinone (yield 61%). Physical data of this compound are shown in Table 1.

후처리

  1. temperaturerefluxed
  2. temperatureby heating for 20 hours in argon atomosphere
  3. temperatureAfter cooling
  4. washwashed with ethyl acetate
  5. extractionThe resultant substance was extracted with ethyl acetate
  6. washthe extract was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:2))

출처 및 근거

ORD 기록
ord-4f02697ac8364430ba92219e21213167
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106858

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