1-Octanol → 5-Bromo-3-chloro-2-(octyloxy)pyridine

HRID 1780065ノート

反応式

HRID 1780065 の反応式
[C:1]([O-:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C(O)CCCCCCC.C([Li])CCC.Br[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([Br:34])=[CH:29][N:28]=1>CCCCCC.O1CCCC1>[Br:34][C:30]1[CH:31]=[C:32]([Cl:33])[C:27]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:28][CH:29]=1

参加物

7

反応物 4

HCID 9571-OctanolHCID 126309832,5-Dibromo-3-chloropyridineHCID 23673717Octanoic acid, lithium salt (1:1)HCID 178418339Butyllithium

生成物 1

HCID 190499905-Bromo-3-chloro-2-(octyloxy)pyridine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

Lithium octanoate (prepared in advance from 13.02 g (100.00 mmol) of 1-octanol and 69 ml (110.00 mmol) of a 1.6 molar n-butyllithium solution in n-hexane in 40 ml of tetrahydrofuran at 0° C.) and 27.13 g (100.00 mmol) of 2,5-dibromo-3-chloropyridine are refluxed for 7 hours in 40 ml of tetrahydrofuran. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the ether phase is washed twice with aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate is freed from the solvent. Chromatographic purification (silica gel/hexane:ethyl acetate 9:1) gives 18.19 g (59.80 mmol) of 5-bromo-3-chloro-2-octyloxypyridine. ##STR21##

後処理

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe ether phase is washed twice with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customChromatographic purification (silica gel/hexane:ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-8c7820111dee488d957c382dab128453
出典データセット
uspto-grants-1997_05
特許番号
US05629428

反応ノート

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