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

HRID 1693888노트

반응식

HRID 1693888 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf4ad7176f954a04abeab825b5d3505f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158657B2

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