Acrylonitrile → 6-fluoro-2H-chromene-3-carbonitrile
反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11](#[N:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1>[OH-].[Na+]>[F:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:10][CH2:13][C:12]([C:11]#[N:14])=[CH:7]2参加物
5
実験手順
A solution of 5-fluoro-2-hydroxybenzaldehyde (1.00 g, 8.92 mmol) and acrylonitrile (9.40 mL, 143 mmol) was refluxed overnight with DABCO (1.00 g, 8.92 mmol). The mixture was cooled and 1 M NaOH (10 mL) was added. The mixture was extracted with EtOAc (20 mL), and the organic layer was dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes) to provide the title compound (4.50 g) as yellow crystals. 1H NMR (300 MHz, CDCl3) δ 7.13 (m, 1H), 6.98 (td, J=8.5, 3.0 Hz, 1H), 6.89-6.80 (m, 2H), 4.80 (d, J=1.4 Hz, 2H).
後処理
- temperatureThe mixture was cooled
- extractionThe mixture was extracted with EtOAc (20 mL)
- dry with materialthe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes)
出典と根拠
- ORDレコード
- ord-bed34000f890428ab403ba851563a5f1
- 出典データセット
- uspto-grants-2014_10
- 特許番号
- US08859584B2
反応ノート
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