Diethyl Ether → HCID 58765692, compound

HRID 860626Notes

Reaction equation

HRID 860626 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:18][CH:19]=[O:20])[CH3:2].[CH3:21][Mg]Br.CCOCC>O1CCCC1>[CH2:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[N:5][C:4]=1[CH2:18][CH:19]([OH:20])[CH3:21])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 85860580HCID 85860580, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58765692HCID 58765692, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetaldehyde (0.253 g, 0.840 mmol), is dissolved in anhydrous tetrahydrofuran (5 mL) and cooled to 0° C. with stirring under nitrogen. Methylmagnesium bromide, 3.0M in ether, (0.300 mL, 1.00 mmol) is added and the ice bath removed. After slowly warming to room temperature, the reaction is monitored by TLC. After the starting material is completely consumed, the reaction is quenched with saturated ammonium chloride solution and diluted with ether. The two phases are separated and the organic washed with water and brine, dried over sodium sulfate, then concentrated. The residue is further purified using flash column chromatography. The 1-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-2-ol (0.222 g, 0.7049 mmol) is formed in 70% yield.

Workup

  1. customthe ice bath removed
  2. temperatureAfter slowly warming to room temperature
  3. customAfter the starting material is completely consumed
  4. customthe reaction is quenched with saturated ammonium chloride solution
  5. additiondiluted with ether
  6. customThe two phases are separated
  7. washthe organic washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue is further purified

Sources & evidence

ORD record
ord-061e2e093b6749e8bea74ec353bca8af
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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