Water → 2-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrile

HRID 333861

反応式

HRID 333861 の反応式
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH2:16][C:17]#[N:18].O>C(O)(C)(C)C>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH:16]([C:3]([C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:12])[C:17]#[N:18]

参加物

5

反応物 3

HCID 962WaterHCID 805662,4-DichlorophenylacetonitrileHCID 586039Methyl 6-methoxypyridine-3-carboxylate

生成物 1

HCID 668131162-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrile収率 29.3%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

To a suspension of potassium-tert-butylate (2.052 g) in tert-butanol (25 ml) was added methyl-6-methoxynicotinate (2.5 g). 2,4-Dichlorobenzyl cyanide (2.782 g) was added portion wise. The mixture was heated to 100° C. for 1.5 h. After cooling to room temperature, water (100 ml) was added and the mixture was washed with diethyl ether. The aqueous phase was neutralized with concentrated aqueous HCl and extracted with EtOAc. The organic phase was washed with water and with brine, dried (MgSO4), filtered and concentrated to dryness to give the title compound (1.407 g) as a yellow foam that was used in the next step without further purification. MS (m/e)=321.0 [M+H+].

後処理

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with diethyl ether
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-9dcae863c2d24463ae9abf9130636ceb
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

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