HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2,2,3,3-Tetrafluoro-1-propanol → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridine

HRID 23321
Notes
Print preview

Reaction equation

HRID 23321 reaction equation
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[H-].[Na+].[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20](OC3N(C)N=C(C(F)(F)F)C=3)[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:4][CH2:3][C:2]([F:8])([F:1])[CH:5]([F:7])[F:6])[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 24758Sodium hydrideHCID 225726302,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine

Product 1

HCID 225726422-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridineYield 99.2%

Reagents, catalysts & solvents 2

HCID 31347
Sulfolane
Solvent
HCID 22335286Ethyl acetate pentaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 2,2,3,3-tetrafluoropropan-1-ol (0.29 g, 2.2 mmol) in dry sulfolane (2 ml) is added NaH (60% in oil, 0.09 g, 2.2 mmol) and 2,6-bis-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine (0.8 g, 1.8 mmol). After stirring at 110° C. for 3.7 h the mixture is cooled to ambient temperature. The resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.72 g, 57% yield) of m.p. 73-74° C.

Workup

  1. temperatureis cooled to ambient temperature
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed 10 times with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Sources & evidence

ORD record
ord-facc9139d28f472d8d74f9b9d1df1032
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852673B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes