Pyridine → 2-(4-Fluorophenyl)-1-phenylethan-1-amine

HRID 2293970ノート

反応式

HRID 2293970 の反応式
CO[N:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.B.C1COCC1.N1C=CC=CC=1.CCOC(C)=O>C1COCC1>[NH2:3][CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 2723981Borane;tetrahydrofuranHCID 54455826HCID 54455826、化合物

生成物 1

HCID 150089772-(4-Fluorophenyl)-1-phenylethan-1-amine収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-(4-fluorophenyl)-1-phenyl-1-ethanone-O-methyl oxime (1.34 g, 4.62 mmol) in 30 ml dry THF under nitrogen was added borane-THF complex (1.0M in THF, 23.1 ml, 23.1 mmol) and dry pyridine (10 ml) by syringe at 25° C. The resulting bi-phasic solution was refluxed with vigorous magnetic stirring for 16 hours. After the reaction was cooled to 25° C. and was quenched with 10% NaOH solution, hexanes (50 ml) were added and the layers were separated. The aqueous portion was extracted with hexanes again (40 ml). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to yield a cloudy colorless syrup (3.55 g, 66% yield for two steps). Rf : 0.24 (EtOAc).

後処理

  1. temperatureThe resulting bi-phasic solution was refluxed with vigorous
  2. customwas quenched with 10% NaOH solution, hexanes (50 ml)
  3. additionwere added
  4. customthe layers were separated
  5. extractionThe aqueous portion was extracted with hexanes again (40 ml)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a cloudy colorless syrup (3.55 g, 66% yield for two steps)

出典と根拠

ORDレコード
ord-d9f4d4017545483bba7f565631882877
出典データセット
uspto-grants-1997_11
特許番号
US05688789

反応ノート

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