2,2,2-Trifluoroethanol → HCID 22923742, compound

HRID 649213Notes

Reaction equation

HRID 649213 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[F:11][C:12]([F:16])([F:15])[CH2:13][OH:14].CC(C)([O-])C.[K+]>>[CH3:10][O:9][C:3]1[C:4]([CH3:8])=[N:5][CH:6]=[CH:7][C:2]=1[O:14][CH2:13][C:12]([F:16])([F:15])[F:11]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 105830464-Chloro-3-methoxy-2-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22923742HCID 22923742, compoundYield 46.8%

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloro-3-methoxy-2-methylpyridine (7.8 g), 2,2,2-trifluoroethanol (24.7 g) and potassium t-butoxide (27.76 g) was heated at 110° C. for 18 hours, then concentrated, diluted with water, and extracted twice with chloroform. The extract was dried, from which chloroform was evaporated, and the residue was purified by column chromatography on silica gel (chloroform-methanol (400:9)), to give 3-methoxy-2-methyl-4-(2,2,2-trifluoroethoxy)pyridine (5.12 g) as a white or pale yellow solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted twice with chloroform
  4. dry with materialThe extract was dried, from which chloroform
  5. customwas evaporated
  6. customthe residue was purified by column chromatography on silica gel (chloroform-methanol (400:9))

Sources & evidence

ORD record
ord-d8e5e26a32364274bc95057786682e38
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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