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

HRID 1242293Notes

Reaction equation

HRID 1242293 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)[CH2:21][CH3:22]>C1COCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:20][CH2:21][CH3:22])=[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 178455855HCID 178455855, compound

Product 1

HCID 21935690[Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-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 (example 3A]) was dissolved in 11.3 ml of abs. THF and treated at −78° C. with 1.2 ml of 2M propyl magnesium chloride solution (in EtOEt, 1.06 eq.). After stirring for 15 Min. at 0° C., the reaction mixture was carefully poured onto crashed ice/NH4Cl, extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) yielded then 0.281 g of the title compound as white crystals of mp. 83–85° C.

Workup

  1. dissolutionwas dissolved in 11.3 ml of abs
  2. additionat 0° C., the reaction mixture was carefully poured
  3. extractionextracted twice with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customFlash chromatography (SiO2, hexane/AcOEt=8/2) yielded

Sources & evidence

ORD record
ord-7f5b14c18e514cf1aa6e0f8afa7934cb
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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