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

HRID 2393185

反応式

HRID 2393185 の反応式
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[C:5]([CH3:15])[C:4]=1[CH:16]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>C(#N)C>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH:16]([C:4]2[C:3](=[O:2])[C:12]3[C:7]([C:6](=[O:13])[C:5]=2[CH3:15])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:29][CH:28]=1

参加物

3

反応物 1

HCID 189792506-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-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 79.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 14.7 g of 6-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-6-(4-methoxyphenyl)hexanoic acid in 300 ml of acetonitrile at 0C was added an aqueous 147 ml solution of 57.2 g of ceric ammonium nitrate portionwisely over 5 min. After stirring for 16 hours at room temperature, the solution was extracted with ethyl acetate. The organic layer was washed, dried, evaporated, and the residue was purified with column chromatography over silica gel using ethyl acetate as an eluent. Recrystallization from isopropyl ether/ethyl acetate gave 10.8 g of the title compound.

後処理

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried
  4. customevaporated
  5. customthe residue was purified with column chromatography over silica gel
  6. customRecrystallization from isopropyl ether/ethyl acetate

出典と根拠

ORDレコード
ord-f527d0de9477491f9d059aa47583a799
出典データセット
uspto-grants-1998_09
特許番号
US05804601

関連ノート

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