2-Bromopyridine → 5-(Pyridin-2-yl)pent-4-yn-1-ol

HRID 654935Notes

Reaction equation

HRID 654935 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:27]([OH:32])[CH2:28][CH2:29][C:30]#[CH:31].[OH-].[Na+]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:31]#[C:30][CH2:29][CH2:28][CH2:27][OH:32]

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 793464-Pentyn-1-ol

Product 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-bromopyridine (5 g, 31.6 mmol), palladium (II) acetate (5 mg), copper (I) iodide (5 mg), triphenylphosphine (5 mg) in triethylamine (40 ml) was deaerated with argon for 5 minutes. After 4-pentyn-1-ol (3.49 ml, 37.9 mmol) was added, the solution was rapidly heated to reflux under argon and conditions maintained for 22 hours. On cooling, the mixture was poured into 2M sodium hydroxide (ca. 30 ml) and extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 60% ethyl acetate/chloroform. Fractions with Rf of about 0.12 on evaporation gave the title alcohol as a pale brown oil.

Workup

  1. temperaturethe solution was rapidly heated
  2. temperatureto reflux under argon
  3. temperatureconditions maintained for 22 hours
  4. temperatureOn cooling
  5. extractionextracted thoroughly with ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulphate)
  8. customextracts gave an oil, which
  9. customchromatographed on silica using 60% ethyl acetate/chloroform
  10. customFractions with Rf of about 0.12 on evaporation

Sources & evidence

ORD record
ord-971fc2b89bb14941ab94843120053329
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…