Potassium Fluoride → 1-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexan-3-ol

HRID 65302노트

반응식

HRID 65302 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].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([C:26]([CH2:32][CH2:33][CH:34]=[O:35])([CH:29]([CH3:31])[CH3:30])[C:27]#[N:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[F-].[K+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:13]([O-:15])=[O:14])[CH:34]([OH:35])[CH2:33][CH2:32][C:26]([C:27]#[N:28])([CH:29]([CH3:30])[CH3:31])[C:20]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 522689Potassium FluorideHCID 30153703-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrileHCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

생성물 1

HCID 137457541-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexan-3-ol수율 73.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 2-(3,4-dimethoxyphenyl)-1-nitroethane (4, 135 g, 0.64 mol), 2-(3,4-dimethoxyphenyl)-2-(3-oxopropyl)-2-isopropylacetonitrile (7, 156 g, 0.57 mol) and KF (19.3 g, anhydrous, Aldrich) in 2-propanol (2.0 L) was heated to 50°-55° C. for about 40 hours. The mixture was then cooled to room temperature and the isopropanol removed in vacuo. The residue was dissolved in CH2Cl2 (1.6 L) and filtered through Celite (50 g). The filtrate was extracted with saturated aqueous NaHCO3 (2×500 mL), the organic layer evaporated, and the product recrystallized from ethyl acetate-hexane (1:1) to yield 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)-hexan-3-ol (8, 205 g, m.p. 171°-173° C., MS m/e 486(M+)).

후처리

  1. temperaturewas heated to 50°-55° C. for about 40 hours
  2. customthe isopropanol removed in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (1.6 L)
  4. filtrationfiltered through Celite (50 g)
  5. extractionThe filtrate was extracted with saturated aqueous NaHCO3 (2×500 mL)
  6. customthe organic layer evaporated
  7. customthe product recrystallized from ethyl acetate-hexane (1:1)

출처 및 근거

ORD 기록
ord-92b6f07b7f574e82a63201563d3f281b
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613606

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