Water → 2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol

HRID 2233551Notes

Reaction equation

[CH2:1]([C:5]1[N:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:8][C:9]=1[CH2:10][C:11](O)=[O:12])[CH2:2][CH2:3][CH3:4].O>O1CCCC1>[CH2:1]([C:5]1[N:6]=[C:7]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)[S:8][C:9]=1[CH2:10][CH2:11][OH:12])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

1.15 g crude [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid were dissolved in 50 ml tetrahydrofuran and cooled in an ice bath to 0° C. At 0° C. 9.3 ml 1 M solution of borane tetrahydrofuran complex were added. The reaction mixture was warmed to 55° C. and stirred for one hour at this temperature. The reaction mixture was cooled in an ice bath and 50 ml water was added. The organic layer was added. The tetrahydrofuran was removed in vacuo and the residue extracted three times with portions of 80 ml ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo to provide 1.1 g crude 2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol as brown oil. This material was used without purification.

Workup

customAt 0° C
temperatureThe reaction mixture was warmed to 55° C.
temperatureThe reaction mixture was cooled in an ice bath
additionThe organic layer was added
customThe tetrahydrofuran was removed in vacuo
extractionthe residue extracted three times with portions of 80 ml ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-5286291971bf4f279c1742890c3204cf
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

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