Diisobutylaluminum hydride → [2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

HRID 1726967Notes

Reaction equation

HRID 1726967 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[CH3:20].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:20][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:18])([F:17])[F:19])=[CH:12][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 670722692-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

Product 1

HCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (3.39 mmol) of the above synthesized 2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester in 7 ml of abs. THF was cooled down to 0° C. and reacted with 7.06 ml of DIBAL-H-solution (1.2 M in toluene, 2.5 eq.) for 1 h. Careful quenching with ice/NH4Cl, twofold extraction with AcOEt, washing with brine, drying over sodium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, hexane/AcOEt=7/3) to deliver finally 0.875 g of the title compound as off-white solid of mp. 76-78° C.

Workup

  1. customCareful quenching with ice/NH4Cl, twofold extraction with AcOEt
  2. washwashing with brine
  3. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  4. waitleft a crude product which
  5. customwas purified by flash chromatography (SiO2, hexane/AcOEt=7/3)

Sources & evidence

ORD record
ord-64a7a59645d345ff8647bc4838dfcb5e
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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