2,2,2-Trifluoro-1-methoxyethanol → HCID 67282369, compound

HRID 913006Notes

Reaction equation

HRID 913006 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][NH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]([CH:27](O)[O:28]C)([F:26])([F:25])[F:24]>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:27]([OH:28])[C:23]([F:26])([F:25])[F:24])=[CH:12][NH:11][C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 98922,2,2-Trifluoro-1-methoxyethanol2×HCID 11430Potassium Carbonate2×HCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 67282369HCID 67282369, compoundYield 37.8%

Conditions

Temperature
120 °C

Procedure

3-Benzyloxy-2-methyl-1H-pyridin-4-one (1 g, 4.64 mmol) was mixed with potassium carbonate (0.2 g, 1.45 mmol) and CF3CH(OCH3)OH (4.34 g, 33.36 mmol) in sealed parallel synthesizer reactor and heated at 120° C. metal block temperature for 2 days. The mixture was cooled, and an additional amount of potassium carbonate (2 g, 14.5 mmol) and CF3CH(OCH3)OH (2 g, 15.30 mmol) was added. The mixture was again heated in a sealed tube at 120° C. for 60 hours. The mixture was cooled to room temperature and then evaporated to dryness. The residual material was purified by column chromatography (5% MeOH:dichloromethane) to give 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (0.55 g, 37.8% yield).

Workup

  1. temperatureThe mixture was cooled
  2. temperatureThe mixture was again heated in a sealed tube at 120° C. for 60 hours
  3. temperatureThe mixture was cooled to room temperature
  4. customevaporated to dryness
  5. customThe residual material was purified by column chromatography (5% MeOH:dichloromethane)

Sources & evidence

ORD record
ord-1baa679bc872461383ac074969416803
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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