Methyl iodide → HCID 22117266, compound

HRID 1872002Notes

Reaction equation

HRID 1872002 reaction equation
[CH2:1]([Li])CCC.[CH3:6][C:7]1([CH3:21])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[N:8]1.CI>CCCCCC.O1CCCC1>[CH3:6][C:7]1([CH3:21])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:19])[CH3:20])=[CH:14][C:13]=2[CH3:1])=[N:8]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10036299HCID 10036299, compoundHCID 178418339Butyllithium

Product 1

HCID 22117266HCID 22117266, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyllithium (52.8 ml of a 2.5M solution in hexane) was added dropwise to a stirred solution of the product of step (i) (27.6 g) in tetrahydrofuran (100 ml) at -20° C. After 2 hours methyl iodide (85.3 g) was added and the mixture was stirred for 2 hours at this temperature then 0.5 hours at room temperature. The reaction mixture was partitioned between brine and ethyl acetate. The aqueous solution was extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5% ethyl acetate in isohexane. Used directly in the next step.

Workup

  1. custom0.5 hours
  2. customat room temperature
  3. customThe reaction mixture was partitioned between brine and ethyl acetate
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customPurification
  8. washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a14fb1d7ff9548b29368b3ce7198a46a
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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