Acrylonitrile → 6-fluoro-2H-chromene-3-carbonitrile
반응식
[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]2참가 물질
5
실험 절차
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).
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-bed34000f890428ab403ba851563a5f1
- 출처 데이터셋
- uspto-grants-2014_10
- 특허 번호
- US08859584B2
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