2,2,2-Trifluoroethanol → HCID 89514299, 화합물

HRID 1778566노트

반응식

HRID 1778566 반응식
[CH3:1][O:2][C:3]1([O:13][CH3:14])[CH2:6][CH:5]([C:7](=O)[CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:4]1.[C:15]([O-:18])(=O)[CH3:16].[NH4+:19].[C:20]([N+:24]#[C-])([CH3:23])([CH3:22])[CH3:21].FC(F)(F)[CH2:28][OH:29]>C(OCC)(=O)C>[C:15]([NH:19][C:7]([CH:5]1[CH2:6][C:3]([O:13][CH3:14])([O:2][CH3:1])[CH2:4]1)([CH2:8][CH2:9][CH:10]=[CH2:11])[C:28]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:29])(=[O:18])[CH3:16]

참가 물질

6

반응물 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 89527308HCID 89527308, 화합물

생성물 1

HCID 89514299HCID 89514299, 화합물수율 79%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1-(3,3-dimethoxycyclobutyl)pent-4-en-1-one (3.0, 15.1) was dissolved in 2,2,2-trifluoroethanol (7 mL). Ammonium acetate (4.66 g, 60.5 mmol) and tert-butyl isocyanide (3.40 mL, 30.3 mmol) were added and the reaction was stirred 3 days at room temperature. The reaction was diluted with ethyl acetate, washed successively with water, saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane to afford the desired product (4.04 g, 79%). Rf 0.16 (50% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 7.10 (br s, 1H), 6.71 (br s, 1H), 5.83-5.69 (m, 1H), 5.03-4.91 (m, 2H), 3.14 (s, 6H), 2.91-2.72 (m, 2H), 2.39-2.24 (m, 2H), 2.13-1.79 (m, 7H), 1.53-1.33 (m, 10H). ESI MS found for C18H32N2O4 m/z [363.0 (M+Na+)].

후처리

  1. washwashed successively with water, saturated aqueous sodium chloride
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-29e66c6028c3464f951c29ee8a769c6d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266908B2

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