2-Bromopyridine → 3-(Pyridin-2-yl)prop-2-yn-1-ol

HRID 654963Notes

Reaction equation

HRID 654963 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=CC=C[CH:9]=1.[OH-:27].[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:9]#[C:8][CH2:13][OH:27]

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 11776TriphenylphosphineHCID 14798Sodium Hydroxide

Product 1

HCID 34811473-(Pyridin-2-yl)prop-2-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 (50 ml) was deaerated with argon for 5 minutes. After propagyl alcohol (2.2 ml, 38.0 mmol) was added, the solution was rapidly heated to reflux under argon and conditions maintained for 17 h. 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 80% ethyl acetate/chloroform. Fractions with Rf of about 0.23 on evaporation gave the title alcohol as a light tan solid: mp 78°-80°.

Workup

  1. temperaturethe solution was rapidly heated
  2. temperatureto reflux under argon
  3. temperatureconditions maintained for 17 h
  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 80% ethyl acetate/chloroform
  10. customFractions with Rf of about 0.23 on evaporation

Sources & evidence

ORD record
ord-919e0253faf74e2e91942a7c466055f4
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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