1-Iodohexane → Dimethyl 2-(4-phenoxyphenyl)-2-n-hexylmalonate

HRID 1386643

Reaction equation

HRID 1386643 reaction equation
[H-].[Na+].[O:3]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C1COCC1>[O:3]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 15540880Dimethyl 2-(4-phenoxyphenyl)malonate

Product 1

HCID 21183037Dimethyl 2-(4-phenoxyphenyl)-2-n-hexylmalonateYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (144 mg of 60% in mineral oil washed with hexanes, 86.4 mg, 3.6 mmol) in dry THF (20 mL) was carefully added dimethyl 2-(4-phenoxyphenyl)malonate (900 mg, 3.0 mmol). The resulting mixture was stirred at room temperature for 1 hour and then 1-iodohexane (1.27 g, 0.89 mL, 6.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and then heated to reflux overnight . The reaction was cooled to room temperature and quenched with 1N HCl (20 mL) and extracted with ether (2×40 mL). The combined organic extracts were washed with saturated Na2S2O3, water, then brine, dried (Na2SO4), concentrated, and purified by chromatography using a Chromatotron with a silica gel plate (4000 micron) eluted with 13% EtOAc/hexanes to give 950 mg of dimethyl 2-(4-phenoxyphenyl)-2-n-hexylmalonate as a viscous oil. 1H NMR (200 mHz, CDCl3) δ 7.39-6.92 (9H, m), 3.75 (6H, s), 2.10 (2H, t), 1.29 (8H, m), 0.87 (3H, t).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe reaction was cooled to room temperature
  5. customquenched with 1N HCl (20 mL)
  6. extractionextracted with ether (2×40 mL)
  7. washThe combined organic extracts were washed with saturated Na2S2O3, water
  8. dry with materialbrine, dried (Na2SO4)
  9. concentrationconcentrated
  10. custompurified by chromatography
  11. washeluted with 13% EtOAc/hexanes

Sources & evidence

ORD record
ord-51c84c1908ed4bb0a55197e469e605b4
Source dataset
uspto-grants-2001_07
Patent number
US06265578B1

Linked notes

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