Potassium Carbonate → 2,2,2-Trifluoro-1-(2-morpholinothiazol-5-yl)ethanol

HRID 1186376

Reaction equation

HRID 1186376 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][C:9]([CH:12]=[O:13])=[CH:10][N:11]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([Si](C)(C)C)([F:23])[F:22]>CN(C)C=O>[F:20][C:21]([F:23])([F:22])[CH:12]([C:9]1[S:8][C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:11][CH:10]=1)[OH:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 14797702-(Morpholin-4-yl)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 674017402,2,2-Trifluoro-1-(2-morpholinothiazol-5-yl)ethanolYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Reference Example 8-2, by use of 2-morpholinothiazole-5-carbaldehyde (177 mg, 0.893 mmol) dissolved in N,N-dimethylformamide (5.3 mL), potassium carbonate (25 mg, 0.18 mmol) and (trifluoromethyl)trimethylsilane (0.198 mL, 1.34 mmol), the mixture was stirred and reacted at room temperature for 2.3 hours. Then, purification by preparative thin-layer chromatography (chloroform/methanol=15/1) was performed to give 2,2,2-trifluoro-1-(2-morpholinothiazol-5-yl)ethanol (Compound DY) (156 mg, yield: 65%).

Workup

  1. customreacted at room temperature for 2.3 hours
  2. customThen, purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-c2161b8b710a4619b109609db1ebd983
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Linked notes

Loading…