Sodium borohydride → 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol

HRID 860623Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde (4.05 g, 12.5 mmol) is dissolved into denatured ethanol (60 mL) at room temperature then cooled to 0° C. in an ice bath. Sodium borohydride (0.467 g, 12.5 mmol) is then carefully added in small portions. The reaction is allowed to warm slowly to room temperature and is monitored by TLC. Upon complete consumption of starting material, the reaction is carefully quenched with water and diluted with ethyl acetate. The ethanol is removed and the residue is extracted with ethyl acetate, washed, dried, and concentrated. The 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol (4.0 g, 12.14 mmol), 97%, is obtained in pure form after flash column chromatography.

Workup

temperatureto warm slowly to room temperature
customUpon complete consumption of starting material
customthe reaction is carefully quenched with water
additiondiluted with ethyl acetate
customThe ethanol is removed
extractionthe residue is extracted with ethyl acetate
washwashed
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-3944b75b31f04891863558b97e70bc42
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153878B2

Reaction notes

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