Diisobutylaluminumhydride → 1-(3,5-Bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1h-[1,2,3]triazole-4-carbaldehyde

HRID 2251981노트

반응식

HRID 2251981 반응식
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([C:18](N2CCOCC2)=[O:19])[N:9]=[N:8]1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[F:32][C:29]([F:30])([F:31])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:28]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([CH:18]=[O:19])[N:9]=[N:8]1

참가 물질

5

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 86601245[1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-morpholin-4-yl-methanone

생성물 1

HCID 877163841-(3,5-Bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1h-[1,2,3]triazole-4-carbaldehyde

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Dissolve [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-morpholin-4-yl-methanone in THF. Cool to −78° C., slowly add 28.3 ml (4 eq) of 1M diisobutyl aluminum hydride in toluene, and stir 2.5 hours. Move to 0° C. ice bath and allow reaction to slowly warm while stirring overnight. Slowly quench by adding ˜5 ml 1N HCl while still at 0° C. then warming to RT. Pour into 50 ml 1N NaOH. Extract with EtOAc, then wash organic layer with 1N HCl. Concentrate organic layer to give the desired aldehyde, which can be used without further purification. MS (IS) 409.2 (M+1). Rf=0.61 (1:1 Hexanes:EtOAc)

후처리

  1. customMove to 0° C.
  2. customreaction
  3. temperatureto slowly warm
  4. customSlowly quench
  5. additionby adding ˜5 ml 1N HCl while still at 0° C.
  6. temperaturethen warming to RT
  7. additionPour into 50 ml 1N NaOH
  8. extractionExtract with EtOAc

출처 및 근거

ORD 기록
ord-3dbc0fb65c3a4801bef192d4de26caf6
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320994B2

반응 노트

불러오는 중…