Methyl iodide → HCID 18689768, compound

HRID 1872018Notes

Reaction equation

HRID 1872018 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=2)=[CH:5][CH:4]=1)[CH3:2].[CH2:16]([Li])CCC.CI>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH2:11][C:12]([CH3:14])([CH3:15])[N:13]=2)=[C:7]([CH3:16])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 128725592-(4-Ethylphenyl)-4,4-dimethyl-2-oxazolineHCID 178418339Butyllithium

Product 1

HCID 18689768HCID 18689768, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product from step (i) (43 g) in tetrahydrofuran (600 ml) at -10° C. was added n-butyllithium (2.5M solution in hexanes, 94 ml). The mixture was stirred for 2.5 hours at 0° C. then cooled to -30° C. and treated with methyl iodide (62 ml). The mixture was warmed to room temperature and partitioned between ethyl acetate and water. The organic phase was dried and evaporated and the residue purified by chromatography eluting with 5% ethyl acetate in isohexane. Yield 28.4 g.

Workup

  1. temperaturethen cooled to -30° C.
  2. temperatureThe mixture was warmed to room temperature
  3. custompartitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe residue purified by chromatography
  7. washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-8e7d705a78104aecabb73958d57bb8c8
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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