Sodium Hydroxide → 1-(5-(4-Chloro-3-(trifluoromethyl)phenyl)furan-2-yl)propan-2-amine

HRID 872531ノート

反応式

HRID 872531 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10](/[CH:13]=[C:14](/[N+:16]([O-])=O)\[CH3:15])=[CH:11][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C(OCC)C.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:13][CH:14]([NH2:16])[CH3:15])=[CH:11][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:20])[F:21]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 70653841(E)-2-(4-chloro-3-(trifluoromethyl)phenyl)-5-(2-nitroprop-1-enyl)furan

生成物 1

HCID 630864961-(5-(4-Chloro-3-(trifluoromethyl)phenyl)furan-2-yl)propan-2-amine収率 47.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

(E)-2-(4-chloro-3-(trifluoromethyl)phenyl)-5-(2-nitroprop-1-enyl)furan (2.58 g, 7.78 mmol) was mixed with diethyl ether (54 ml) and toluene (25 ml) and added drop wise to a cooled (−20° C.) solution of lithium aluminium hydride (2.5 g, 65.9 mmol) in diethyl ether (11 ml). The mixture was allowed to warm up to 0° C. and stirred for 3 h and then at RT for additional 1 h stirring. Then the mixture was cooled again and 2.5 ml of water was added at −30° C. and then 2.5 ml of 15% aqueous NaOH solution. An additional 7.5 ml of water was added and the solution was allowed to warm to RT. MgSO4 was added and the mixture was stirred and filtered, precipitate was washed with toluene and diethyl ether and the filtrate was evaporated to dryness. After CombiFlash purification with DCM:MeOH as eluent system, the pooled fractions afforded 1.13 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.01 (d, 3H), 2.63 (m, 2H), 3.11-3.15 (m, 1H) 6.28 (d, 1H), 7.07 (d, 1H), 7.68 (d, 1H), 7.87 (m, 1H), 7.95 (m, 1H).

後処理

  1. additionadded drop wise to
  2. stirringat RT for additional 1 h stirring
  3. temperatureThen the mixture was cooled again
  4. temperatureto warm to RT
  5. stirringthe mixture was stirred
  6. filtrationfiltered
  7. washprecipitate was washed with toluene and diethyl ether
  8. customthe filtrate was evaporated to dryness
  9. customAfter CombiFlash purification with DCM

出典と根拠

ORDレコード
ord-b47e29f393764537a1730cc08a5a07de
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

反応ノート

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