Methyl iodide → HCID 59504617, compound

HRID 2400552Notes

Reaction equation

HRID 2400552 reaction equation
[OH:1][C:2]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.[H-].[Na+].[CH3:16]I>CN(C=O)C.O>[CH3:16][O:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=2)[CH2:3][O:4][CH2:5]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59504645HCID 59504645, compound2×

Product 1

HCID 59504617HCID 59504617, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-hydroxyoxetan-3-yl)benzonitrile (Step 1 of Intermediate O, 600 mg, 3.43 mmol) in DMF (12.5 mL) was added sodium hydride (60% suspension in mineral oil, 151 mg, 3.77 mmol) at a temperature of ˜5° C. The reaction mixture was allowed to stirr for 1 h at this temperature, before methyl iodide (256 μL, 4.11 mmol) was added. Stirring was continued at rt over night. The mixture was diluted with water and extracted with diethyl ether. The organic extract was dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 20:1→4:1) to afford the title compound in pure form (566 mg, 87%): 1H NMR (500 MHz, DMSO-d6) δ 7.93 (d, 2H), 7.68 (d, 2H), 4.81 (d, 2H), 4.73 (d, 2H), 3.05 (s, 3H); ES-MS m/z 190 (MH)+; HPLC RT (Method E) 1.22 min.

Workup

  1. additionwas added
  2. waitwas continued at rt over night
  3. extractionextracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customAfter evaporation of the solvent
  8. customthe crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 20:1→4:1)

Sources & evidence

ORD record
ord-dd633d16035249aab46880206bfa0a93
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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