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

HRID 2251981ノート

反応式

HRID 2251981 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-3dbc0fb65c3a4801bef192d4de26caf6
出典データセット
uspto-grants-2008_01
特許番号
US07320994B2

反応ノート

読み込み中…