2,2,2-Trifluoroethanol → HCID 90204115, compound

HRID 1480165Notes

Reaction equation

HRID 1480165 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1.[F:13][C:14]([F:18])([F:17])[CH2:15][OH:16].CC(C)([O-])C.[K+]>CN(C=O)C>[F:13][C:14]([F:18])([F:17])[CH2:15][O:16][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 23665647Potassium tert-butoxideHCID 90203880HCID 90203880, compound

Product 1

HCID 90204115HCID 90204115, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-chloropyridin-3-yl)cyclobutanol (Example 108a, 0.83 g, 4.52 mmol) in dry DMF (20 ml) under an argon atmosphere was added 2,2,2-trifluoroethanol (CAN 75-89-8, 904 mg, 653 μl, 9.04 mmol) and potassium tert-butoxide (533 mg, 4.75 mmol). The reaction mixture was stirred at room temperature for 20 minutes and stirred at 90° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/(solution 3% Et3N in ethylacetate) to yield the title compound (885 mg, 71%) as a yellow oil. MS (ESI, m/z): 248.5 (M+H+).

Workup

  1. stirringstirred at 90° C. for 18 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethylacetate
  4. extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
  5. customThe organic phase was collected
  6. dry with materialdried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a heptane/(solution 3% Et3N in ethylacetate)

Sources & evidence

ORD record
ord-df03473b8b424bdfa3313226f15996ea
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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