2,2,2-Trifluoroethanol → 126764-32-7

HRID 1192972Notes

Reaction equation

HRID 1192972 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].CC(C)([O-])C.[K+].Cl[C:14]1[N:18]([CH3:19])[N:17]=[C:16]([CH3:20])[C:15]=1[CH:21]=[O:22]>C1COCC1.ClCCl>[CH3:19][N:18]1[C:14]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[C:15]([CH:21]=[O:22])[C:16]([CH3:20])=[N:17]1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 14998085126764-32-7Yield 109.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2,2-Trifluoroethanol (7.11 ml, 97.6 mmol) was added dropwise to potassium tert-butoxide (1M in THF) (97.6 ml, 97.6 mmol) at 0° C. A solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (10.3 g, 65.1 mmol) in THF (28 ml) was added slowly to the solution at 0° C. The solution was allowed to warn to room temperature and stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and concentrated to give the product as a yellow oil (15.82 g, 109% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3): 2.42 (s, 3H, Me), 3.65 (s, 3H, Me), 4.93 (q, 2H, CH2), 9.72 (s, 1H, CH).

Workup

  1. customto warn to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8fdcb23a0b7749e8b0497a53c569662e
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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