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

HRID 232056

反応式

HRID 232056 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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]-1,4-benzoquinone (yield 61%). Physical data of this compound are shown in Table 1.

後処理

  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))

出典と根拠

ORDレコード
ord-fc042433dfd945ce90f7ef3e446fbb3f
出典データセット
uspto-grants-1989_07
特許番号
US04851413

関連ノート

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