Dimethylformamide → 3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

HRID 1426165ノート

反応式

HRID 1426165 の反応式
[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13](Cl)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32].CN(C=O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13]([O:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Cl:25])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 673694373-(Benzyloxy)-5-chloro-2-nitropyridine

生成物 1

HCID 673694033-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine収率 54.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-(benzyloxy)-5-chloro-2-nitropyridine (1.00 g, 3.78 mmol), potassium carbonate (2.09 g, 15.1 mmol), 2-chlorophenol (1.46 g, 11.3 mmol) and DMF (16 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled, partitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL). The organic layer was washed with 2N NaOH (30 mL), water, and brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.73 g, 54.2% yield) as a light yellow solid. 1H NMR (CDCl3) δ 5.16 (s, 2H), 6.90 (s, 1H), 7.09 (d, 1H), 7.28-7.37 (m, 7H), 7.52 (d, 1H), 7.72 (s, 1H).

後処理

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL)
  3. washThe organic layer was washed with 2N NaOH (30 mL), water, and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC (Biotage)
  7. washeluting with 5:1 hexane

出典と根拠

ORDレコード
ord-27019af157bc4f0d8690ad89af05e1d3
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

反応ノート

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