Diethyl Ether → 2-Benzyl-6-methoxypyridine

HRID 1359264

反応式

HRID 1359264 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].C(OCC)C.Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[N:17]=1>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[CH2:1]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 2568102-Bromo-6-methoxypyridineHCID 5462224Magnesium

生成物 1

HCID 219422742-Benzyl-6-methoxypyridine

試薬・触媒・溶媒 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A Grignard's reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethylether was slowly added dropwise into a mixture of 150 g of 2-bromo-6-methoxypyridine, 4.3 g of 1,3-bis(diphenylphosphino)propanenickel(II) chloride and 500 ml of tetrahydrofuran under stirring in an ice bath. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic phase was washed with water and then brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 1% and 1.5% of ethyl acetate/hexane, to give 150 g of the target compound.

後処理

  1. stirringAfter stirring overnight as it
  2. extractionthe mixture was extracted with an aqueous ammonium chloride solution and hexane
  3. washThe organic phase was washed with water
  4. dry with materialbrine, dried over anhydrous magnesium sulfate
  5. customthe solvent was removed

出典と根拠

ORDレコード
ord-3545b138c24840c7a248a5339a693d9e
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

関連ノート

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