Water → 3-(2,4-Dichloro-phenyl)-1,1,1-trifluoro-2-[2-(2-hydroxy-ethoxy)-pyridin-4-yl]-butan-2-ol

HRID 333819Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH3:14])[CH:9]=[CH:8][N:7]=1.[Li+].[BH4-].O>C1COCC1.Cl>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH:13]([CH3:14])[C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([O:5][CH2:4][CH2:3][OH:2])[CH:11]=1)([OH:27])[C:23]([F:26])([F:25])[F:24]

Participants

Conditions

Temperature: 45 °C

Procedure

{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester (Example 120, 70 mg) was dissolved in THF (5 mL) and treated with LiBH4 (10 mg). After 2 h stirring at 45° C. another portion of LiBH4 (5 mg) was added and the reaction mixture further stirred at 45° C. for 2 h. After cooling down to r.t., 3 drops of 1N aqueous HCl were added, followed by water (5 mL). The reaction mixture was then extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 30:70) to give the title compound as colorless foam (52 mg). MS (m/e)=410.3 (MH+).

Workup

additionwas added
temperatureAfter cooling down to r.t.
extractionThe reaction mixture was then extracted twice with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 30:70)

Sources & evidence

ORD record: ord-a8bf3e9e7d084056b3bdaf9cf296abdc
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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