Methyl iodide → HCID 20040843, compound

HRID 1053594Notes

Reaction equation

HRID 1053594 reaction equation
[CH2:1]([N:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[C:20]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH2:1]([N:3]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:20])=[CH:9][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71735772HCID 71735772, compound

Product 1

HCID 20040843HCID 20040843, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3 (78 mg, 0.3 mmol), K2CO3 (95 mg, 0.69 mmol), in acetone (50 mL), 1 mL (16 mmol) of MeI was added. The reaction mixture was heated to reflux for 48 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 50 mL water. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/CH2Cl2 (2/1) to provide compound 24 (49 mg, 0.18 mmol, 60% yield) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.23 (m, 2H), 6.83 (m, 4H), 6.73 (d, J=8.4 Hz, 2H), 6.68 (t, J=7 Hz, 1H), 4.07 (t, J=6.4 Hz, 2H), 3.77 (s, 3H), 3.70 (t, J=6.4 Hz, 2H), 3.47 (q, J=7 Hz, 2H), 1.20 (t, J=7 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 153.93, 152.91, 147.62, 129.38, 115.95, 115.40, 114.67, 111.80, 66.01, 55.74, 49.76, 45.59, 12.30; HRMS (ESI, positive) m/z calcd. For C17H22NO2 [M+H]+: 272.1645, found: 272.1646.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 hr
  3. customthe solvent was evaporated
  4. customthe residue was quenched with 50 mL water
  5. extractionThe mixture was then extracted with EtOAc
  6. washthe combined organic layer was washed with water
  7. dry with materialbrine, and dried over Na2SO4
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography with hexane/CH2Cl2 (2/1)

Sources & evidence

ORD record
ord-99e9dc58886b470b88cbca3edb8a4c55
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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