Methyl iodide → HCID 131714225, compound

HRID 463054Notes

Reaction equation

HRID 463054 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]1(/[C:19](/[C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CI.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][CH:24]([CH2:23][CH2:22][CH2:21]/[CH:20]=[C:19](\[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)/[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 13417302HCID 13417302, compoundHCID 178418339Butyllithium

Product 1

HCID 131714225HCID 131714225, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of diisopropylamine (0.21 ml, 1.46 mmole) in tetrahydrofurane (3 ml) was cooled at -60° C. under argon, and a hexane solution of n-butyl lithium (1.6M, 0.92 ml, 1.46 mmole) was added dropwise to the solution. After stirring for 10 minutes, a solution of methyl (E)-7-phenyl-7-(3-pyridyl)-6-heptenoate (360 mg, 1.22 mmole) in tetrahydrofuran (2 ml) was added dropwise to the solution, followed by stirring at -60° to -70° C. for 20 minutes. Subsequently, methyl iodide (0.12 ml, 1.83 mmole) was added, and the reaction was allowed to proceed at the same temperature for 1 hour. Saturated aqueous ammonium chloride was added to the reaction mixture, and the product was extracted with ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated. The residue was chromatographed on silica gel, and development was effected with isopropyl ether:ethyl acetate (7:3) to yield methyl (E)-2-methyl-7-phenyl- 7-(3-pyridyl)-6-heptenoate (3-a) (270 mg, 71.6 %).

Workup

  1. stirringby stirring at -60° to -70° C. for 20 minutes
  2. waitto proceed at the same temperature for 1 hour
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel, and development

Sources & evidence

ORD record
ord-0eb4321ed1af432f8401bb6562230eb4
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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