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

HRID 256193

반응식

HRID 256193 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35b6b33fe63b4760957d68c62003f647
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04701461

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