Hydrochloric Acid → 1-(3,4-Dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone

HRID 1249510ノート

反応式

HRID 1249510 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N+:13]([O-:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].I[CH2:17][CH2:18][C:19](=[O:30])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.Cl.[N+](C([N+]([O-])=O)=O)([O-])=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:13]([O-:15])=[O:14])[CH2:17][CH2:18][C:19](=[O:30])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-HCID 130650191-Iodo-5-(4-methoxyphenyl)-3-pentanoneHCID 54223030Nitro ketone

生成物 1

HCID 130650201-(3,4-Dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 15 g. (0.071 mole) of 2-(3,4-dimethoxyphenyl)-1-nitroethane in 200 ml. of dry tetrahydrofuran was added 33.45 g. (0.08 mole) of 40% Triton B at room temperature. The solution was stirred at room temperature for 14 minutes under N2. 22.6 g. (0.071 mole) of 1-iodo-5-(4-methoxyphenyl)-3-pentanone was then added in portions. The mixture was heated at 50°-55° for 2 hours under N2 until no more starting material was detected on TLC, and then cooled to room temperature. The resulting reaction solution was poured into cold dil. HCl and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. The crude material was chromatographed on Florisil to provide 22 g. of desired nitro ketone derivative. Recrystallization from 80% ethanol gave a white solid which has m.p. 87°-89° C.

後処理

  1. customat room temperature
  2. temperatureThe mixture was heated at 50°-55° for 2 hours under N2 until
  3. temperaturecooled to room temperature
  4. customThe resulting reaction solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. customThe crude material was chromatographed on Florisil
  8. customto provide 22 g
  9. customRecrystallization from 80% ethanol
  10. customgave a white solid which

出典と根拠

ORDレコード
ord-4a990e0d76a243aaa862b9683d48b64e
出典データセット
uspto-grants-1986_12
特許番号
US04632929

反応ノート

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