Dimethylformamide → HCID 22040099, compound

HRID 858858Notes

Reaction equation

HRID 858858 reaction equation
[Li]CCCC.CN([CH:9]=[O:10])C.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][C:20]=1Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][C:24]=1[CH:9]=[O:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14631589HCID 14631589, compoundHCID 178418339Butyllithium

Product 1

HCID 22040099HCID 22040099, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (7.56 mL, 18.9 mmol, 2.5M in hexanes) followed by DMF (5.5 mL) were added to a cooled −78° C. solution of 1-benzyloxy-2-bromo-4-ethyl-benzene (5 g, 17.2 mmol) in THF (40 mL). The reaction was stirred at −78° C. for 1 hr and then warmed up to rt. After 2 hrs the reaction was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (0% to 5% EtOAc in hexanes) gave the title compound as a clear oil (3.6 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.8 Hz, 3 H), 2.62 (q, J=7.8 Hz, 2 H), 5.17 (s, 2 H), 6.97 (d, J=8.6 Hz, 1 H), 7.33–7.45 (m, 6 H), 7.69 (s, 1 H), 10.54 (s, 1 H).

Workup

  1. temperaturewarmed up to rt
  2. customAfter 2 hrs the reaction was quenched with 1N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a yellow oil
  7. customPurification by flash column chromatography (0% to 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-24b5ebb8933741d9a8cd57aaa3bb4b7a
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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