Methanol → HCID 67292192, compound

HRID 1685410Notes

Reaction equation

HRID 1685410 reaction equation
[C:1]1([C:7]2[C:12]([F:13])=[CH:11][C:10]([O:14]CC3C=CC=CC=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C(OCC)(=O)C.[OH-].[Na+]>[Pd].C(O)(=O)C>[F:13][C:12]1[CH:11]=[C:10]([OH:14])[CH:9]=[N:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67293036HCID 67293036, compound

Product 1

HCID 67292192HCID 67292192, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6.55 g (29.7 mM) of 2-phenyl-3-fluoro-5-(phenylmethoxy)pyridine are added to 160 ml of methanol, 30 ml of ethyl acetate and 30 ml of acetic acid. 0.33 g of 10% palladium-on-charcoal is added. The mixture is stirred under a hydrogen atmosphere for 3 hours. The catalyst is filtered off and the solvents are concentrated to give a white solid, which is taken up with 1 N sodium hydroxide solution. The aqueous phase obtained is washed with dichloromethane and then acidified to pH 5 with 1 N hydrochloric acid solution. The white precipitate obtained is filtered off and washed with water. After drying, the desired product is obtained in the form of a white solid with a yield of 77%.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solvents are concentrated
  3. customto give a white solid, which
  4. customThe aqueous phase obtained
  5. washis washed with dichloromethane
  6. customThe white precipitate obtained
  7. filtrationis filtered off
  8. washwashed with water
  9. customAfter drying

Sources & evidence

ORD record
ord-c04c4cc7fb3e4c11947c3f9eb6dc5796
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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