Methyl iodide → HCID 90112538, compound

HRID 1508773Notes

Reaction equation

HRID 1508773 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][CH:9]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:27]>CN(C=O)C.O>[CH3:27][C:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:23][CH:22]=1)([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90110274HCID 90110274, compound

Product 1

HCID 90112538HCID 90112538, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 250-mL round bottom flask was charged with diisopropyl 2-(4-nitrobenzyl)malonate (1.61 g, 4.98 mmol) in DMF (24 mL). To this solution at 0° C. was slowly added NaH (60% suspension, 0.24 g, 5.97 mmol). After 30 minutes, iodomethane (0.37 mL, 5.97 mmol) was added in one portion. The reaction was stirred for 21 h, at which time, the reaction was warmed to rt. The reaction was diluted in water (250 mL) and extracted with methyl tert-butylether (3×75 mL). The combined extract was washed with saturated sodium chloride (2×20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica using hexanes/ethyl acetate (10:0 to 8:2) as eluent to afford the title compound (1.44 g, 86%) as a white solid. MW=337.37. 1H NMR (CDCl3, 300 MHz) δ 8.16-8.09 (m, 2H), 7.37-7.30 (m, 2H), 5.05 (sept, J=6.3 Hz, 2H), 3.30 (s, 2H), 1.33 (s, 3H), 1.27-1.20 (m, 12H).

Workup

  1. customat 0° C.
  2. extractionextracted with methyl tert-butylether (3×75 mL)
  3. extractionThe combined extract
  4. washwas washed with saturated sodium chloride (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-d4ea17455af845948ffcece5cf5110a0
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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