2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde → [Rac]-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

HRID 1726969Notes

Reaction equation

HRID 1726969 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][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:3]=1.[CH3:20][Mg]Cl>C1COCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH3:20])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:19])[F:18])=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 219359652-Methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 69035957[Rac]-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.470 g (1.77 mmol) of the above prepared 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde was dissolved in 9 ml of abs. THF and treated at −10° C. with 0.89 ml of 3M methyl magnesium chloride solution (in THF). After 15 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 to leave 0.508 g of the title product, pure according to NMR.

Workup

  1. dissolutionwas dissolved in 9 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-caacd75d1fc54eb8b0222727b40b0d14
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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