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

HRID 1726975Notes

Reaction equation

HRID 1726975 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[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][CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 690396242-Methyl-6-(3-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester

Product 1

HCID 21935815[2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.96 g (6.62 mmol) of the above synthesized 2-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester in 14 ml of abs. THF was cooled down to 0° C. and reacted with 13.8 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=55/45) to deliver finally 1.66 g of the title compound as white crystals of mp. 75-77° 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=55/45)

Sources & evidence

ORD record
ord-70b95057c0ac4a9ca24eda39452ff2ee
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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