Benzyl Bromide → 2-Benzyl-6-methoxypyridine

HRID 2216338

反応式

HRID 2216338 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.O1CCCC1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Mg]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C>[CH2:15]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 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 3283Diethyl Ether溶媒

実験手順

While stirring 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 in an ice bath, Grignard reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethyl ether was added dropwise slowly. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography with (1% ethyl acetate/hexane and 1.5% ethyl acetate/hexane), to give 150 g of the title compound.

後処理

  1. additionwas added dropwise slowly
  2. stirringAfter stirring overnight as it
  3. extractionthe mixture was extracted with an aqueous ammonium chloride solution and hexane
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, dried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel column chromatography with (1% ethyl acetate/hexane and 1.5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-cb11222e764849c083897a8941c8501e
出典データセット
uspto-grants-2006_09
特許番号
US07112593B2

関連ノート

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