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

반응식

HRID 2393185 반응식
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

참가 물질

3

반응물 1

HCID 189792506-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)-6-(4-methoxyphenyl)hexanoic acid

생성물 1

HCID 152308586-(3-Methyl-1,4-naphthoquinon-2-yl)-6-(4-methoxyphenyl)hexanoic acid수율 79.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f527d0de9477491f9d059aa47583a799
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05804601

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