Aluminium lithium hydride → 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

HRID 253205Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17])C>C1COCC1>[OH:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17]

Participants

Conditions

Temperature: 5 °C

Procedure

Cool (0° C.) a solution of lithium aluminum hydride (5.3 mL, IM in THF) and add a solution of [5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (Example 1, 1.4 g, 4.25 mmol) in THF (15 mL). On complete addition, remove the cold bath and stir for 2 hrs. Cool this solution to 5° C., and then add water (0.2 mL), dropwise, followed by NaOH solution (0.2 mL, 5M in water) and water (0.2 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. Purify the residue by flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane) to give the title compound as a yellow solid (0.879 g) Use the compound of Example 1 as the starting material to obtain the title compound.

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
customPurify the residue
washby flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane)

Sources & evidence

ORD record: ord-ab20c3bdc8af44b5afd89ae4774a77fb
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872032B2

Reaction notes

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