Menadiol → 6-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid

HRID 1464493

反応式

HRID 1464493 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:13].C(O[CH:17]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])C>CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3](=[O:13])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:12])[C:11]=1[CH:17]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]

参加物

5

反応物 2

HCID 10209MenadiolHCID 190880606-Ethoxy-6-(4-methoxyphenyl)hexanoic acid

生成物 1

HCID 152308586-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid収率 45%

試薬・触媒・溶媒 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-触媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

D-Camphor-10-sulfonic acid (0.1 g) was added to a toluene solution (50 ml) of 2-methyl-1,4-naphthohydroquinone (3.6 g, 0.02 mole) and 6-ethoxy-6-(4-methoxyphenyl)hexanoic acid (5.6 g, 0.021 mole), and the mixture was heated at 60° C. for 18 hours, with stirring. After cooling, the solvent was distilled off under reduced pressure, and then tetrahydrofuran (20 ml) was added to the residue. A 10% aqueous solution of ferric chloride was added to the solution, followed by stirring for 10 minutes, and the reaction product was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a silica gel column, and elution was effected with isopropyl ether to give 6-(3-methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid (3.5 g, 45%). This product was recrystallized from isopropyl ether. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound No. 21 was prepared.

後処理

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. additiontetrahydrofuran (20 ml) was added to the residue
  4. additionA 10% aqueous solution of ferric chloride was added to the solution
  5. stirringby stirring for 10 minutes
  6. extractionthe reaction product was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was chromatographed on a silica gel column, and elution

出典と根拠

ORDレコード
ord-11f17cfa6af24ad39d782efb78fd64a7
出典データセット
uspto-grants-1994_04
特許番号
US05304658

関連ノート

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