Sodium hydride → 4-(6-Fluoro-pyridin-2-yloxymethyl)-benzonitrile

HRID 1693888ノート

反応式

HRID 1693888 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[OH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[H-].[Na+]>CN(C)C=O>[F:8][C:4]1[N:3]=[C:2]([O:9][CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 160549p-Cyanobenzyl alcohol

生成物 1

HCID 592552944-(6-Fluoro-pyridin-2-yloxymethyl)-benzonitrile収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To an N,N-dimethylformamide (50 mL) solution of 2,6-difluoropyridine (5 g, 43.4 mmol) and 4-(hydroxymethyl)benzonitrile (8.67 g, 65.1 mmol) was added sodium hydride (2.56 g, 65.1 mmol, 60% in oil) at room temperature. This mixture was stirred for 4 hours at 70° C. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1-4:1) to obtain the title compound (5.99 g, 61%).

後処理

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1-4:1)

出典と根拠

ORDレコード
ord-cf4ad7176f954a04abeab825b5d3505f
出典データセット
uspto-grants-2012_04
特許番号
US08158657B2

反応ノート

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