Cesium carbonate → N-ethyl-5-(furan-3-yl)-2-methylaniline

HRID 1964015

反応式

HRID 1964015 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9].[O:12]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:8]([NH:7][C:6]1[CH:10]=[C:2]([C:14]2[CH:15]=[CH:16][O:12][CH:13]=2)[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:9]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 437296995-bromo-N-ethyl-2-methylaniline

生成物 1

HCID 66877311N-ethyl-5-(furan-3-yl)-2-methylaniline収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 22 hours
  3. customAfter completion of the reaction, filtration
  4. customcondensed
  5. customThe resulting crude product was separated
  6. custompurified

出典と根拠

ORDレコード
ord-6f317208b33b4f2a8539517b604f631b
出典データセット
uspto-grants-2013_04
特許番号
US08415479B2

関連ノート

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