Water → {5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol

HRID 585073Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14](OCC)=[O:15])[CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][OH:15])[CH:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 5-[4-(trifluoromethyl)phenyl]isoxazole-3-carboxylate (130 mg) was dissolved in ethanol (10 ml), cooled to 0° C., and sodium borohydride (26 mg) was added in portions to the stirred solution. The mixture was stirred at room temperature for 4 hours, then excess water added. Solvent was evaporated under reduced pressure, and the residue was purified by preparative thin layer chromatography, eluting with 5% methanol/ethyl acetate, to provide {5-[4-(trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol, a compound of formula (24).

Workup

customSolvent was evaporated under reduced pressure
customthe residue was purified by preparative thin layer chromatography
washeluting with 5% methanol/ethyl acetate

Sources & evidence

ORD record: ord-acd12eab6f3041ce97aac3d6d7a3d28c
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930111B2

Reaction notes

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