2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde → [Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol

HRID 1726977Notes

Reaction equation

HRID 1726977 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.[CH2:20]([Mg]Cl)[CH3:21]>C1COCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:20][CH3:21])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:19])[F:18])[CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 219356242-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehydeHCID 178461633HCID 178461633, compound

Product 1

HCID 69039637[Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.600 g (2.26 mmol) of the above prepared 2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde was dissolved in 11 ml of abs. THF and treated at −15° C. with 1.08 ml of 2.5 M ethyl magnesium chloride solution (in THF). After 30 Min., the reaction mixture was carefully poured onto crashed ice/NH4Cl, extracted twice with AcOEt, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) produced finally 0.473 g of pure title compound as white crystals of mp. 97-99° C.

Workup

  1. dissolutionwas dissolved in 11 ml of abs
  2. addition, the reaction mixture was carefully poured
  3. extractionextracted twice with AcOEt
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0483ee356cfb4f1f9bdf4baa65fa6b7f
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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