3'-(Trifluoromethyl)acetophenone → 2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

HRID 1242289Notes

Reaction equation

HRID 1242289 reaction equation
[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:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.CC(C1C=CC=C(C(F)(F)F)C=1)=O>C(Cl)Cl.O=[Mn]=O>[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:18])([F:17])[F:19])[CH:11]=2)[N:3]=1

Participants

5

Reactant 2

HCID 676823'-(Trifluoromethyl)acetophenoneHCID 21935815[2-Methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

Product 1

HCID 219356242-Methyl-6-(3-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

3.00 g (11.2 mmol) of [2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (synthesized as described in example 1K]-M], but starting with 3-(trifluoromethyl) acetophenone instead of 4-(trifluoromethyl) acetophenone), was dissolved in 56 ml of CH2Cl2 and treated with 14.6 g (15 eq.) of MnO2. After vigorous stirring for 2 h at ambient temperature, the reaction mixture was filtered over Celite and carefully rinsed with CH2Cl2. Evaporation of the solvent left 2.659 g of the title compound as white crystals of mp. 61–63° C.

Workup

  1. filtrationthe reaction mixture was filtered over Celite
  2. washcarefully rinsed with CH2Cl2
  3. customEvaporation of the solvent
  4. waitleft 2.659 g of the title compound as white crystals of mp. 61–63° C.

Sources & evidence

ORD record
ord-1f4ffd9524044db796ab73fcc018fafb
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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