6-(4-(Trifluoromethyl)phenyl)picolinaldehyde → 3-Methyl-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-butanol

HRID 1391762Notes

Reaction equation

HRID 1391762 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>CCOCC.C([Mg]Br)C(C)C>[CH3:2][CH:3]([CH3:8])[CH2:4][CH:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:1])[F:18])=[CH:8][CH:7]=2)[N:14]=1)[OH:16]

Participants

4

Reactant 1

HCID 247300896-(4-(Trifluoromethyl)phenyl)picolinaldehyde

Product 1

HCID 586298133-Methyl-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-butanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 178418816HCID 178418816, compoundSolvent

Procedure

Prepared from 6-[4-(trifluoromethyl)phenyl]-2-pyridinecarbaldehyde (500 mg, 1.99 mmol) in Et2O (20 mL) and isobutylmagnesium bromide (1.1 mL of a 2M solution in Et2O, 2.2 mmol) according to the procedure used for the preparation of Intermediate 47 to give, after purification by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 4:1) the title compound as a white crystalline solid (215 mg).

Workup

  1. customto give
  2. customafter purification by SPE (silica, 10 g cartridge)
  3. washeluting with cyclohexane

Sources & evidence

ORD record
ord-5192f9156d58497c9a00d048bcf09144
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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