2,2,3,3,3-Pentafluoropropanol → HCID 20142800, compound

HRID 649214Notes

Reaction equation

HRID 649214 reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][OH:4].CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[C:18]=1[O:24][CH3:25]>C(OCC)(=O)C>[CH3:25][O:24][C:18]1[C:19]([CH3:23])=[N:20][CH:21]=[CH:22][C:17]=1[O:4][CH2:3][C:2]([F:9])([F:1])[C:5]([F:8])([F:7])[F:6]

Participants

5

Reactant 3

HCID 98722,2,3,3,3-PentafluoropropanolHCID 105830464-Chloro-3-methoxy-2-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 20142800HCID 20142800, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2,2,3,3,3-pentafluoropropanol (21 ml) were added in small portions, potassium tert-butoxide (23.6 g) and then 4-chloro-3-methoxy-2-methyl-pyridine (7.5 g). After being refluxed for 40 hours, the reaction mixture was cooled, to which ethyl acetate was added and the insoluble substance was filtered off. The filtrate was concentrated and purified by column chromatography, to give 3-methoxy-2-methyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine (1.7 g) as a light yellow oil while 4.1 g of the starting material was recovered at the same time.

Workup

  1. temperatureAfter being refluxed for 40 hours
  2. additionwas added
  3. filtrationthe insoluble substance was filtered off
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-236e55094be14c168daeafee9d0a941d
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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