Hydrochloric Acid → 3-Pyridinebutanol

HRID 1656311Notes

Reaction equation

HRID 1656311 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][CH2:9][CH2:10][O:11]C2CCCCO2)[CH:2]=1.Cl>CO.O.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 539444502-[4-(3-Pyridyl)but-3-enoxy]tetrahydropyran

Product 1

HCID 134191363-PyridinebutanolYield 241.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

10 g (43 mmol) of 2-[4-(3-pyridyl)but-3-enoxy]tetrahydropyran in 200 ml of methanol/water 1:1 (v/v) is acidified by 2N hydrochloric acid and hydrogenated for 16 hours over 2 g 10% palladium on carbon. After filtration, the solvent is removed, the remaining residue is neutralized by saturated aqueous bicarbonate, and the product is extraced with several portions of ether. Purification of the crude product by column chromatography on silica gel yields 15.7 g (87%) of 4-(3-pyridyl)but-Anol as colourless viscous oil. (C9H13NO; F.W. 151.2).

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed
  3. customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record
ord-f25440d9186642c1840fccd1a2b923db
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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