[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol → 2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

HRID 1242473Notes

Reaction equation

HRID 1242473 reaction equation
C(OC(=O)CCC1C=CC(O)=CC=1C)C.ClC(C1C(C)=NC(C2C=CC(C(F)(F)F)=CC=2)=CC=1)CC(C)C.[CH3:39][C:40]1[C:45]([CH2:46][OH:47])=[CH:44][CH:43]=[C:42]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)[N:41]=1>O=[Mn]=O>[CH3:39][C:40]1[C:45]([CH:46]=[O:47])=[CH:44][CH:43]=[C:42]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:55])[F:57])=[CH:50][CH:49]=2)[N:41]=1

Participants

5

Reactant 3

HCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanolHCID 21935943[Rac]-3-(1-chloro-3-methyl-butyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

Product 1

HCID 219359652-Methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

In analogy to the procedures described in examples 8A] and 31B], 3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 60B]) was reacted with [rac]-3-(1-chloro-3-methyl-butyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (prepared from [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (example 1M]) by i) oxidation with MnO2 in analogy to the procedure described in example 3A] to yield 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbaldehyde; ii) treatment with isobutyl magnesium chloride and iii) reaction with SOCl2 in analogy the procedures described in examples 4A] and 4B]) to give [rac]-3-(2-methyl-4-{3-methyl-1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butoxy}-phenyl)-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow solid.

Sources & evidence

ORD record
ord-c073ba6b74de4fbb85054d916f326f90
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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