Diethyl Ether → (3-Bromo-phenyl)-cyclopropyl-methyl-amine

HRID 2377435ノート

反応式

HRID 2377435 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:11])[CH:9]=O)[CH:5]=[CH:6][CH:7]=1.[CH2:12]([Mg]Br)[CH3:13].CCOCC.C(OCC)(=O)C>O1CCCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH:9]2[CH2:13][CH2:12]2)[CH3:11])[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 12030886N-(3-Bromo-phenyl)-N-methyl-formamide2 回HCID 178418443HCID 178418443、化合物

生成物 1

HCID 21107154(3-Bromo-phenyl)-cyclopropyl-methyl-amine収率 15%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A stirred, cooled (0° C.) solution of N-(3-bromo-phenyl)-N-methyl-formamide (Intermediate 112, 2.6 g, 9.7 mmol) and titanium tetra-iso-propoxide (3.9 mL, 10.67 mmol) in tetrahydrofuran (40 mL) was treated with a 3M solution of ethyl magnesium bromide in ether (8.08 mL, 24.25 mmol) under argon and the resulting reaction mixture was allowed to warm to ambient temperature gradually and refluxed at 55° C. overnight. It was then cooled in an ice-bath, quenched with saturated aqueous ammonium chloride solution, filtered over celite and the aqueous phase was extracted with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil. Flash column chromatography over silica gel (230-400 mesh) using 1.5% ethyl acetate in hexane as the eluent afforded the title compound (0.321 g, 15%).

後処理

  1. customthe resulting reaction mixture
  2. temperaturerefluxed at 55° C. overnight
  3. temperatureIt was then cooled in an ice-bath
  4. customquenched with saturated aqueous ammonium chloride solution
  5. filtrationfiltered over celite
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto afford an oil

出典と根拠

ORDレコード
ord-c2f37b4cc9d840ad8f9aae26b30a7944
出典データセット
uspto-grants-2008_12
特許番号
US07468391B2

反応ノート

読み込み中…