4-Methylpyridine → HCID 18446302, compound

HRID 854015Notes

Reaction equation

HRID 854015 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[Li+].CC([N-][CH:13]([CH3:15])[CH3:14])C.C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.C1(Br)CC1.[NH4+].[Cl-]>C1COCC1>[CH:13]1([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 79634-MethylpyridineHCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 18446302HCID 18446302, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of 4-picoline (1.1 g, 11.8 mmol) in THF (5 mL) was added a solution of LDA 2M in THF/heptane/ethylbenzene (Aldrich) (5.9 mL, 11.8 mmol) the resulting reaction mixture was stirred at −78° C. for 3 h then −40° C. for 1 h. Then cyclopropyl bromide (1.43 g, 11.8 mmol) was added at −78° C., let it warm up to room temperature and stirred at room temperature for 1 h. To the reaction mixture was added saturated aqueous NH4Cl (10 mL) the aqueous phase was extracted with EtOAc (10×2 mL) and the combined organic extracts dried over Na2SO4. The solvent was removed and the product 4-cyclopropylmethylpyridine (0.5 g, 31%) was obtained and used without further purification.

Workup

  1. customthe resulting reaction mixture
  2. wait−40° C. for 1 h
  3. temperaturewarm up to room temperature
  4. stirringstirred at room temperature for 1 h
  5. extractionwas extracted with EtOAc (10×2 mL)
  6. dry with materialthe combined organic extracts dried over Na2SO4
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-f35d58db9b2a44178dbcf974d3eb357d
Source dataset
uspto-grants-2007_08
Patent number
US07256177B2

Reaction notes

Loading…