6-(4-(Trifluoromethyl)phenyl)nicotinaldehyde → (6-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanol

HRID 1669238Notes

Reaction equation

HRID 1669238 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:19][CH2:20][Mg+].[Br-]>C1COCC1>[F:18][C:2]([F:17])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([OH:16])[CH2:19][CH3:20])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 219364496-(4-(Trifluoromethyl)phenyl)nicotinaldehydeHCID 178461630HCID 178461630, compound

Product 2

HCID 21935952(6-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanolHCID 597294191-[6-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde (2.1 g, 8.3 mmol) in THF (20 mL) is added EtMgBr (3.0 M in Et2O, 3.2 mL, 9.6 mmol) at 0˜5° C., stirred for 2 hrs, quenched by NH4Cl aq., extracted with ethyl acetate, dried and concentrated giving 1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol (1.8 g) and [6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (0.29 g).

Workup

  1. customquenched by NH4Cl aq.
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-71d643e386a049fb8c7a40f6aefe9a6e
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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