2-Hydroxyisobutyric acid → 2-Methyl-2-(5-(trifluoromethyl)pyridin-2-yloxy)propanoic acid

HRID 2104281Notes

Reaction equation

HRID 2104281 reaction equation
[H-].[Na+].[OH:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6].Cl[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1.ClC1C=C(C(F)(F)F)C=CN=1>>[CH3:8][C:4]([O:3][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1)([CH3:9])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 116712-Hydroxyisobutyric acidHCID 24758Sodium hydrideHCID 222705672-Chloro-4-trifluoromethylpyridine 2-chloro-5-trifluoromethylpyridine

Product 1

HCID 160983422-Methyl-2-(5-(trifluoromethyl)pyridin-2-yloxy)propanoic acid

Procedure

The title compound was prepared following the procedure described in Reference Example 36, Step A with 1.5 extra equivalent of sodium hydride substituting lithium lactate with hydroxyisobutyric acid and 2-chloro-4-trifluoromethylpyridine 2-chloro-5-trifluoromethylpyridine. 1H NMR (500 MHz, CD3OD): δ 8.38 (br, 1H), 7.94 (dd, 1H), 6.93 (d, 1H), 1.69 (s, 6H).

Sources & evidence

ORD record
ord-6395adf27db04cdc82a96e8548063b80
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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