2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde → [2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

HRID 1242290Notes

Reaction equation

HRID 1242290 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.C[Mg]Cl>C1COCC1>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 219356242-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 21935815[2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.500 g (1.89 mmol) of the above prepared 2-methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde was dissolved in 9.4 ml of abs. THF and treated at −10° C. with 0.94 ml of 3M methyl 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, dried over sodium sulfate, and evaporated to dryness to leave 0.532 g of the title product, pure according to NMR.

Workup

  1. dissolutionwas dissolved in 9.4 ml of abs
  2. addition, 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

Sources & evidence

ORD record
ord-74950623264f439a9ef3f0974e9a6f9e
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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