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

HRID 890435Notes

Reaction equation

HRID 890435 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

g (3.39 mmol) of 2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester in 7 ml of abs. THF were 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 0.875 g of the title compound as off-white solid, 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-934c78e6060f4c1cb4c6cf7cca28abb3
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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