Diisobutylaluminum hydride → HCID 21935842, compound

HRID 1242346Notes

Reaction equation

HRID 1242346 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 21935842HCID 21935842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-cdc5cf6842ba41a094c20865215cd980
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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