Dimethylformamide → 6-Phenoxynicotinaldehyde

HRID 78289

反応式

HRID 78289 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C([Li])CCC.CN(C)[CH:22]=[O:23]>O1CCCC1>[O:8]([C:5]1[N:6]=[CH:7][C:2]([CH:22]=[O:23])=[CH:3][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 223468455-Bromo-2-phenoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 27765006-Phenoxynicotinaldehyde収率 32%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromo-2-phenoxy-pyridine described in Manufacturing Example 231-1-1 (18.7 g, 74.6 mmol) in tetrahydrofuran (360 mL) was added n-butyl lithium (31.1 mL, 2.64 M hexane solution, 82.1 mmol) under nitrogen atmosphere at −78° C., which was stirred for 30 minutes at −78° C. To this reaction solution was added N,N-dimethylformamide (7.46 mL, 97 mmol) at −78° C., which was stirred for 1 hour at this temperature. The reaction solution was partitioned into ethyl acetate and water. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (4.75 g, 32%).

後処理

  1. stirringwhich was stirred for 1 hour at this temperature
  2. customThe reaction solution was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-e63b264174214bd89303b46794ad14bb
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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