Ethanol → HCID 178516524, compound

HRID 375057Notes

Reaction equation

HRID 375057 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[CH:7]=[CH:6][N:5]=1.C(O)C.[H][H]>[Pd].CCCCCC>[F:18][CH:2]([F:1])[O:3][C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 189941322-Difluoromethoxy-4-benzyloxypyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 178516524HCID 178516524, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8058HexaneSolvent

Procedure

2-Difluoromethoxy-4-benzyloxypyridine (219.75 g, 0.875 mol), ethanol (500 mL) and palladium on carbon (7.8 g, 5 mol %, 50% by weight water) were shaken on a Parr hydrogenator at 5393 kPa of hydrogen at RT for 2.5 h. The mixture was then filtered through celite and the solvent was evaporated in-vacuo. 2-Difluoromethoxy-4-hydroxypyridine (123 g, 87% yield) was obtained as a white solid after trituration with hexane, mp=88.6° C. -89.8° C. Anal. Calcd. for C6H5NO2F2 : C,44.73; H,3.13; N,8.69 Found: C,44.82; H,3.13; N,8.76.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. customthe solvent was evaporated in-vacuo

Sources & evidence

ORD record
ord-229a7940610e4ff3acf105f9192dc5b7
Source dataset
uspto-grants-1996_01
Patent number
US05484761

Reaction notes

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