5-Ethynyl-2-methylpyridine → 3-Acetyl-6-methylpyridine

HRID 1183783

Reaction equation

HRID 1183783 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)#[CH:2].C1(C)C=CC=CC=1.S(=O)(=O)(O)[OH:18]>>[CH3:9][C:6]1[N:7]=[CH:8][C:3]([C:1](=[O:18])[CH3:2])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 6381975-Ethynyl-2-methylpyridineHCID 22282551HCID 22282551, compound

Product 1

HCID 952923-Acetyl-6-methylpyridineYield 2,704.3%

Conditions

Temperature
50 °C

Procedure

1.0 g 5-ethynyl-2-methylpyridine (8.5 mmol) was loaded into a flask provided with magnetic anchor and was dissolved in 10 mL of a 1:4 toluene/sulfuric acid mixture (0.29 mmol). The resulting solution was heated to 50° C. overnight, then after quenching to room temperature, the solution was basified by the addition of NaHCO3, then it was extracted with AcOEt (3×20 mL) and finally, anhydrified on anhydrous MgSO4. The organic phase was then concentrated under vacuum yielding 1.06 g product, equal to a molar yield of 91% as a yellow oil.

Workup

  1. customprovided with magnetic anchor
  2. customafter quenching to room temperature
  3. additionthe solution was basified by the addition of NaHCO3
  4. extractionit was extracted with AcOEt (3×20 mL)
  5. concentrationThe organic phase was then concentrated under vacuum

Sources & evidence

ORD record
ord-56f35e875ee7416bb36eec67165659a1
Source dataset
uspto-grants-2014_03
Patent number
US08664402B2

Linked notes

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