Aluminium lithium hydride → {2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

HRID 585069Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylate (1.365 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C., and lithium aluminum hydride in tetrahydrofuran (1.365 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, slowly quenched with water, followed by addition of ammonium chloride solution. The resulting mixture was filtered through celite, and washed with ethyl acetate. The filtrate was washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by chromatography, to yield {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methan-1-ol, a compound of formula (16).

Workup

customslowly quenched with water
additionfollowed by addition of ammonium chloride solution
filtrationThe resulting mixture was filtered through celite
washwashed with ethyl acetate
washThe filtrate was washed with brine
dry with materialdried over sodium sulfate, and solvent
customremoved under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-95a36d3e4df243e68f8c87cb79d836a2
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930111B2

Reaction notes

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