2,2,2-Trifluoroethanol → HCID 89514299、化合物

HRID 1778566ノート

反応式

HRID 1778566 の反応式
[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]

参加物

6

反応物 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 89527308HCID 89527308、化合物

生成物 1

HCID 89514299HCID 89514299、化合物収率 79%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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+)].

後処理

  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

出典と根拠

ORDレコード
ord-29e66c6028c3464f951c29ee8a769c6d
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

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