Methyl iodide → HCID 58303914, compound

HRID 1404127Notes

Reaction equation

HRID 1404127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([O:16][CH2:17][CH3:18])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C:12]([O:14][CH3:15])=[O:13].[C:20]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([O:16][CH2:17][CH3:18])=[C:6]2[C:10]=1[N:9]([CH3:20])[CH:8]=[C:7]2[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58303877HCID 58303877, compound

Product 1

HCID 58303914HCID 58303914, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 30-10 (2 g, 7 mmol) in acetone (40 mL) was added K2CO3 (3 g, 21 mmol) and MeI (1.2 g, 8.4 mmol). The reaction mixture was refluxed overnight before it was cooled to room temperature. The solid was filtered off and the filtrate was evaporated to give the crude product, which was purified on silica gel column chromatography eluting with hexane/ethyl acetate (1:5) to afford 30-11 (1.4 g, 67%) as a yellow solid. LRMS: calc 299.1 and found: 300.1 [M+1].

Workup

  1. temperatureThe reaction mixture was refluxed overnight before it
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated
  4. customto give the crude product, which
  5. customwas purified on silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (1:5)

Sources & evidence

ORD record
ord-f2593097479e4142a095410206d0b8e8
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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