4-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acid → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

HRID 2103420Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:11][C:12]=1[C:13](O)=[O:14]>C1COCC1>[CH3:7][C:8]1[N:9]=[C:10]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=2)[S:11][C:12]=1[CH2:13][OH:14]

Participants

Conditions

Temperature: 5 °C

Procedure

Cool (0° C.) a solution of lithium aluminum hydride (10 mL, 1M in THF) and add a solution of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid (Commercially available, 2.87 g, 10 mmol) in THF (20 mL). On complete addition, remove the cold bath and stir for 3.5 hrs. Cool this solution to 5° C., and then add water (0.25 mL), dropwise, followed by NaOH solution (0.25 mL, 5M in water) and water (0.5 mL). Dilute the resulting mixture with ethyl acetate and then filter through a pad of celite. Wash the solids with dichloromethane and then concentrate the combined filtrates under reduced pressure to give the title compound as a yellow solid (2.59 g).

Workup

additionOn complete addition
customremove the cold bath
additionDilute the resulting mixture with ethyl acetate
filtrationfilter through a pad of celite
washWash the solids with dichloromethane
concentrationconcentrate the combined filtrates under reduced pressure

Sources & evidence

ORD record: ord-8e591d076a4e4f399ff4b411751d1582
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576109B2

Reaction notes

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