Potassium Carbonate → Pentyl 4-(3,4-dicyanophenoxy)benzoate

HRID 39207

反応式

HRID 39207 の反応式
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[OH:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:22]([O:21][C:19]([C:18]1[CH:27]=[CH:28][C:15]([O:14][C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])=[CH:16][CH:17]=1)=[O:20])[CH2:23][CH2:24][CH2:25][CH3:26]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 23019Pentyl 4-hydroxybenzoateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

生成物 1

HCID 68981262Pentyl 4-(3,4-dicyanophenoxy)benzoate収率 85%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-nitrophthalonitrile (1.00 g, 7 mmol), pentyl 4-hydroxybenzoate (1.45 g, 7 mmol) and dried potassium carbonate (6.38 g, 46.2 mmol) in anhydrous DMF (50 mL) was stirred overnight at 85° C. under argon. After cooling to room temperature, the mixture was diluted with ethyl acetate (60 mL) and water (40 mL). The organic layer was separated, and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL) and dried over anhydrous sodium sulfate. The solvents were removed in vacuo, and the crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent to give the product in 85% yield. [1H NMR (δ, ppm, CDCl3): 8.15 (d, 2H, J=8.7 Hz), 7.77 (d, 1H, J=8.7 Hz), 7.35 (d, 1H, J=2.3 Hz), 7.30 (d, 1H, J=8.7 Hz), 7.12 (d, 2H, J=8.7 Hz), 4.34 (2H, t, OCH2, J=6.7 Hz), 1.79 (m, 2H, CH2), 1.42 (m, 4H, CH2CH2), 0.94 (t, 3H, J=7 Hz, CH3).]

後処理

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customthe crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent
  8. customto give the product in 85% yield

出典と根拠

ORDレコード
ord-55bb5dca550f4cd6ac687da0cbf92ba2
出典データセット
uspto-grants-2013_09
特許番号
US08524891B2

関連ノート

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