Triisopropyl borate → 2-Octyloxy-5-pyridineboronic acid

HRID 1757029ノート

反応式

HRID 1757029 の反応式
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.C([O:25][B:26](OC(C)C)[O:27]C(C)C)(C)C>C(OCC)C.CCCCCC>[CH2:1]([O:9][C:10]1[N:11]=[CH:12][C:13]([B:26]([OH:27])[OH:25])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

6

反応物 3

HCID 21531Triisopropyl borateHCID 144392315-bromo-2-(octyloxy)PyridineHCID 178418339Butyllithium

生成物 1

HCID 224127982-Octyloxy-5-pyridineboronic acid

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-75 °C

実験手順

2.75 g (10 mmol) of 2-octyloxy-5-bromopyridine are dissolved in 60 ml of absolute diethyl ether, and the solution is cooled to -75° C. under inert gas. 16 mmol of 1.6M butyllithium solution in hexane are added, and the mixture is additionally stirred at -75° C. for 15 minutes. 4.5 g of triisopropylborate in 50 ml of absolute diethyl ether are then added dropwise. The cooling device is then removed. After the batch has warmed to room temperature, 50 ml of 10% HCl are added, and the mixture is additionally stirred at room temperature for 30 minutes. The phases are separated, and the organic phase is washed twice with saturated NaCl solution. The solvent is distilled off in vacuo, and the residue is recrystallized from acetonitrile, giving 6-octyloxypyridine-3-boronic acid.

後処理

  1. customThe cooling device is then removed
  2. temperatureAfter the batch has warmed to room temperature
  3. addition50 ml of 10% HCl are added
  4. stirringthe mixture is additionally stirred at room temperature for 30 minutes
  5. customThe phases are separated
  6. washthe organic phase is washed twice with saturated NaCl solution
  7. distillationThe solvent is distilled off in vacuo
  8. customthe residue is recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-7291f1ffde824df6887bf39092a43130
出典データセット
uspto-grants-1995_08
特許番号
US05443754

反応ノート

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