Isopropanol → HCID 20191879, 화합물

HRID 2119072노트

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HRID 2119072 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])(C(C)C)[C:27]#[N:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[F-].[K+].[CH3:38][CH:39](O)[CH3:40]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:39]([CH3:40])[CH3:38])[CH:12]([N+:13]([O-:15])=[O:14])[CH:34]([OH:35])[CH2:33][CH2:32][CH:26]([C:27]#[N:28])[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

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HCID 3776IsopropanolHCID 522689Potassium FluorideHCID 30153703-(3,4-Dimethoxyphenyl)-2-methyl-6-oxohexane-3-carbonitrileHCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

생성물 1

HCID 20191879HCID 20191879, 화합물

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-(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-529d1b29ff6d48b6bfa3b07021f22a82
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04681889

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