Potassium Carbonate → α-(Trifluoromethyl)-5-thiazolemethanol

HRID 1186360Notes

Reaction equation

HRID 1186360 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]([Si](C)(C)C)([F:17])[F:16]>CN(C)C=O>[F:14][C:15]([F:17])([F:16])[CH:6]([C:5]1[S:1][CH:2]=[N:3][CH:4]=1)[OH:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 27735771,3-Thiazole-5-carbaldehyde

Product 1

HCID 67130512α-(Trifluoromethyl)-5-thiazolemethanolYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Reference Example 8-2, by use of thiazole-5-carbaldehyde (300 mg, 2.65 mmol) dissolved in N,N-dimethylformamide (4.5 mL), potassium carbonate (73 mg, 0.53 mmol) and (trifluoromethyl)trimethylsilane (0.470 mL, 3.18 mmol), the mixture was stirred and reacted at room temperature for 1 hour. Then, purification by preparative thin-layer chromatography (chloroform/methanol=15/1) was performed to give 2,2,2-trifluoro-1-(thiazol-5-yl)ethanol (Compound DL) (353 mg, yield: 73%).

Workup

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

Sources & evidence

ORD record
ord-df420f343dc44b449eaf79c98d639630
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…