2,2,2-Trifluoro-1-methoxyethanol → HCID 70805135, compound

HRID 1519050Notes

Reaction equation

HRID 1519050 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[C:6]([OH:9])=[CH:5][N:4]([CH3:10])[C:3]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].C[O:19][CH:20](O)[C:21]([F:24])([F:23])[F:22]>CO>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([OH:9])=[C:5]([CH:20]([OH:19])[C:21]([F:24])([F:23])[F:22])[N:4]([CH3:10])[C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 11430Potassium CarbonateHCID 66898486HCID 66898486, compound

Product 1

HCID 70805135HCID 70805135, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

3-Chloro-5-hydroxy-1,2-dimethylpyridin-4(1H)-one (500 mg, 2.80 mmol) was suspended in trifluoroacetaldehyde methyl hemiacetal (3 mL). Potassium carbonate (119 mg, 0.86 mmol) was added and the mixture was heated to 120° C. After 2.5 hours, the reaction mixture was allowed to cool to room temperature, then diluted with methanol and filtered. The filtrate was concentrated to dryness and diluted with acetone. The solution was filtered and the filtrate was concentrated to give 3-chloro-5-hydroxy-1,2-dimethyl-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (650 mg) as a pink solid. Yield=85%; 1H-NMR (MeOD-D4, 90 MHz) δ (ppm): 5.9 (q, J=9.1 Hz, 1H), 4.01 (s, 3H) and 2.65 (s, 3H); MS-ESI m/z 272 [M+1]+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness
  4. additiondiluted with acetone
  5. filtrationThe solution was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7e0675da0d7a4cf1899bc64702cdc042
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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