Diisobutylaluminum hydride → HCID 21935842, 화합물

HRID 1242346노트

반응식

HRID 1242346 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 21935842HCID 21935842, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cdc5cf6842ba41a094c20865215cd980
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115611B2

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