Methyl iodide → HCID 67354237, compound

HRID 2369225Notes

Reaction equation

HRID 2369225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:8]=3[NH:9][C:10]=2[CH:11]=1.[OH-].[Na+].I[CH3:22]>C1C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:8]=3[N:9]([CH3:22])[C:10]=2[CH:11]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 67352385HCID 67352385, compound

Product 1

HCID 67354237HCID 67354237, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 29a (60.1 mg, 0.26 mmol) in benzene (2 mL) was added aqueous sodium hydroxide (50% by mass, 540 μL), tetrabutylammonium iodide (50 mg, 0.14 mmol), and iodomethane (130 μL, 2.09 mmol). The reaction mixture was stirred vigorously at 40° C. for 16 hours and then at 55° C. for 2 additional hours. Upon cooling to room temperature, the mixture was diluted with benzene (10 mL) and H2O (10 mL), and the aqueous layer was extracted 2×10 mL ethyl acetate. Organic layers were combined, washed 1×15 mL H2O, dried over anhydrous magnesium sulfate and concentrated to yield a brown solid. Crude product was purified by flash column chromatography (20:1 to 10:1 hexanes—ethyl acetate) to give a tan brown solid in 64% yield (40 mg, 0.16 mmol). 1H NMR (600 MHz, CDCl3): δ 7.60 (d, 1H, J=7.8 Hz), 7.51-7.52 (m, 2H), 7.32-7.34 (t, 1H, J=7.2 Hz), 7.18-7.20 (t, 1H, J=7.2 Hz), 6.84-6.85 (m, 2H), 3.98 (s, 3H), 3.93 (s, 3H), 3.66 (s, 2H); 13C NMR (150 MHz, CDCl3): δ 156.0, 147.6, 143.8, 142.7, 135.7, 126.4, 125.4, 123.9, 120.3, 119.6, 118.7, 116.9, 108.9, 93.8, 55.7, 31.1, 30.1. FTIR: cm−1 2935, 1605, 1566, 1492, 1385, 1310, 1263, 1230, 1210, 1040, 812, 755. EI-HRMS: Calcd. for C17H15NO+ [M]+: 249.1154. found 249.1158.

Workup

  1. customat 55° C.
  2. temperatureUpon cooling to room temperature
  3. extractionthe aqueous layer was extracted 2×10 mL ethyl acetate
  4. washwashed 1×15 mL H2O
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto yield a brown solid
  8. customCrude product was purified by flash column chromatography (20:1 to 10:1 hexanes—ethyl acetate)
  9. customto give a tan brown solid in 64% yield (40 mg, 0.16 mmol)

Sources & evidence

ORD record
ord-0f66c54ae6b74ae8886b510e611c360f
Source dataset
uspto-grants-2014_04
Patent number
US08703936B2

Reaction notes

Loading…