Water → HCID 59527249, compound

HRID 384475Notes

Reaction equation

HRID 384475 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=1.[OH-:16].[Na+].O>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CO>[O:13]1[CH2:14][CH2:15][CH:10]([CH2:9][O:8][C:6]2[CH:7]=[C:2]([OH:16])[CH:3]=[N:4][CH:5]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 64205470HCID 64205470, compound

Product 1

HCID 59527249HCID 59527249, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 3-bromo-5-(tetrahydro-2H-pyran-4-ylmethoxy)pyridine (300 mg), copper(II) sulfate pentahydrate (130 mg), bronze (100 mg), sodium hydroxide (700 mg), and water (5 mL) was stirred in an autoclave at 210° C. for 6 hours. The reaction mixture was cooled to room temperature, followed by addition of methanol, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure and extracted with chloroform. The aqueous layer was neutralized by addition of 1M hydrochloric acid (3.5 mL), followed by extraction with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 5-(tetrahydro-2H-pyran-4-ylmethoxy)pyridin-3-ol (137 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwere removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. extractionextracted with chloroform
  5. additionThe aqueous layer was neutralized by addition of 1M hydrochloric acid (3.5 mL)
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0556670fcbe9438d97c47293dac555dd
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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