Diisobutylaluminum hydride → HCID 21935842、化合物

HRID 1242346ノート

反応式

HRID 1242346 の反応式
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:7][C:6]=1[CH:21]1[CH2:23][CH2:22]1)C.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:21]1([C:6]2[C:5]([CH2:4][OH:3])=[CH:10][CH:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=3)[N:7]=2)[CH2:23][CH2:22]1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 670722652-Cyclopropyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester

生成物 1

HCID 21935842HCID 21935842、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.193 g (0.576 mmol) of the above prepared 2-cyclopropyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester in 3.0 ml of abs. THF was cooled down to 0° C. and reacted with 1.5 ml of DIBAL-H-solution (1.0 M in toluene, 2.6 eq.) for 1 h. Careful quenching with ice, filtration over Celite, separation of the layers, reextraction of the aqueous phase with AcOEt, washing of the combined organic layers with NH4Cl, and drying over magnesium sulfate was followed by evaporation of the solvents. The crude product was finally purified by flash chromatography (SiO2, hexane/AcOEt=7/3) to deliver 0.128 g of the title compound as white crystals.

後処理

  1. customCareful quenching with ice, filtration over Celite, separation of the layers, reextraction of the aqueous phase with AcOEt
  2. washwashing of the combined organic layers with NH4Cl
  3. dry with materialdrying over magnesium sulfate
  4. customwas followed by evaporation of the solvents
  5. customThe crude product was finally purified by flash chromatography (SiO2, hexane/AcOEt=7/3)

出典と根拠

ORDレコード
ord-cdc5cf6842ba41a094c20865215cd980
出典データセット
uspto-grants-2006_10
特許番号
US07115611B2

反応ノート

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