Acrylonitrile → 6-Trifluoromethoxy-2H-chromene-3-carbonitrile

HRID 1697457

反応式

HRID 1697457 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.[C:15](#[N:18])[CH:16]=[CH2:17].C1N2CCN(CC2)C1>CCOCC>[F:12][C:11]([F:14])([F:13])[O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:17][C:16]([C:15]#[N:18])=[CH:4]2

参加物

5

反応物 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

生成物 1

HCID 669452446-Trifluoromethoxy-2H-chromene-3-carbonitrile収率 49.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
130 °C

実験手順

To a microwave tube was added 2-hydroxy-5-trifluoromethoxybenzaldehyde (1 g, 5.0 mmol), 2-propenenitrile (1.6 mL, 24.3 mmol) and triethylenediamine (136 mg, 1.2 mmol). The reaction was heated in the microwave at 130° C. for 1 hour. After cooling, the resulting solution was diluted with ether (100 mL) and washed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 15% EtOAc in hexanes over 1 hour) gave the product (600 mg) as a solid. m/z=242.4 (M+1), r.t.=3.72 mins. 1H NMR (400 MHz; CDCl3) δ 7.14-7.12 (2H, m), 7.00 (1H, s), 6.89 (1H, d), 4.85 (2H, s).

後処理

  1. temperatureAfter cooling
  2. washwashed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9b24365928e2465c918785947e07515b
出典データセット
uspto-grants-2012_04
特許番号
US08163901B2

関連ノート

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