Ethyl Acetate → 4-(Diethylboranyl)pyridine

HRID 240218

反応式

HRID 240218 の反応式
[Li+].CCC[CH2-].Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13]([B:15]([CH2:18][CH3:19])OC)[CH3:14].C(OCC)(=O)C>CCOCC.[Cl-].[Na+].O>[CH2:13]([B:15]([CH2:18][CH3:19])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH3:14]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 142684-BromopyridineHCID 61028n-Butyl lithiumHCID 522516Diethylmethoxyborane

生成物 1

HCID 133188714-(Diethylboranyl)pyridine

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-40 °C

実験手順

N-Butyllithium (1.6M in hexanes, 20 ml) was added to dry ether (100 ml) and cooled to −40° C. under nitrogen. The solution was stirred and a solution of 4-Bromopyridine (32 mmols) dissolved in dry ether was added drop wise. The ethereal solution was stirred for 30 minutes at −40° C. then cooled to −70° C. Diethyl methoxy borane (4.6 ml) dissolved in dry ether (50 ml) was added drop wise and the mixture was allowed to warm to room temperature over night. Ethyl acetate (100 ml) and brine (70 ml) were added to the resulting brown solution and the organic layer was separated. This was dried over magnesium sulfate, filtered and evaporated to yield a brown tar. The product was purified by column chromatography on silica eluted with toluene to yield (0.94 g, 6.4 mmols) of Diethyl (4-pyridyl borane) (I) as a white solid.

後処理

  1. additionwas added drop wise
  2. stirringThe ethereal solution was stirred for 30 minutes at −40° C.
  3. temperaturethen cooled to −70° C
  4. additionwas added drop wise
  5. temperatureto warm to room temperature over night
  6. customthe organic layer was separated
  7. dry with materialThis was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield a brown tar
  11. customThe product was purified by column chromatography on silica
  12. washeluted with toluene

出典と根拠

ORDレコード
ord-5f209412a0e34e0d8cf7cf77a42a0b89
出典データセット
uspto-grants-2014_02
特許番号
US08647827B2

関連ノート

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