4-Methylpyridine → HCID 18446301, compound

HRID 1269115Notes

Reaction equation

HRID 1269115 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.C1[CH2:20][O:19]CC1.CCCCCCC.C(C1C=CC=CC=1)C.C1(Br)CC1.[NH4+].[Cl-].C1C[O:45]CC1>>[CH:13]1([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[C:2]([C:20]([OH:19])=[O:45])[CH:3]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 6

HCID 79634-MethylpyridineHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 78037BromocyclopropaneHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 18446301HCID 18446301, compoundYield 31%

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. Cyclopropyl bromide (1.43 g, 11.8 mmol) was added at −78° C., the reaction mixture was allowed to warm up to room temperature and was 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. 4-Cyclopropylmethylpyridine-2-carboxylic acid (0.5 g, 31%) was obtained after the solvent was removed and used without further purification.

Workup

  1. customThe resulting reaction mixture
  2. wait−40° C. for 1 h
  3. temperatureto warm up to room temperature
  4. stirringwas stirred at room temperature for 1 h
  5. extractionthe aqueous phase was extracted with EtOAc (10×2 mL)
  6. dry with materialthe combined organic extracts dried over Na2SO4

Sources & evidence

ORD record
ord-e9e9f863f9aa4be286d0514d1151272b
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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