Water → HCID 59634012, compound

HRID 1615084Notes

Reaction equation

HRID 1615084 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH:10]([N-]C(C)C)([CH3:12])[CH3:11].[Li+].C(Br)C=C.O>O1CCCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[CH2:1]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1)[CH2:12][CH:10]=[CH2:11]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 887392-Cyano-4-methylpyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 59634012HCID 59634012, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-methylpyridine-2-carbonitrile (2.0 g) in THF (60 mL) was added 2.0 M LDA in heptane/THF/ethylbenzene (10.2 mL) at −78° C. The mixture was stirred at −78° C. for 2 hr. Allyl bromide (2.4 g) was added to the mixture at −78° C. The reaction mixture was stirred at −78° C. for 2.5 hr and at RT for 12 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=9/1) to give the title compound (0.34 g, 12%).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 2.5 hr and at RT for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-ae38fc2d0af94f988fbdcd8a25d5f6cb
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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