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

HRID 872531노트

반응식

HRID 872531 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-b47e29f393764537a1730cc08a5a07de
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975254B2

반응 노트

불러오는 중…