Diisobutylaluminum hydride → HCID 21935720, compound

HRID 1242364Notes

Reaction equation

HRID 1242364 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20][O:21][CH3:22].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:22][O:21][CH2:20][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 670723702-Methoxymethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Product 1

HCID 21935720HCID 21935720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.364 g (1.119 mmol) of the above prepared 2-methoxymethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester in 6 ml of abs. THF was cooled down to 0° C. and reacted with 2.8 ml of DIBAL-H-solution (1.0 M in toluene, 2.5 eq.) for 1 h. Careful quenching with icewater, filtration over a pad of Celite, twofold extraction with AcOEt, washing with NH4Cl-solution, drying over magnesium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, hexane/AcOEt=1/1) to yield finally 0.312 g of the title compound as colorless oil.

Workup

  1. customCareful quenching with icewater, filtration over a pad of Celite, twofold extraction with AcOEt
  2. washwashing with NH4Cl-solution
  3. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  4. waitleft a crude product which
  5. customwas purified by flash chromatography (SiO2, hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-9bbe5a85fffa452e87fc4d32d6af13b2
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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