HCID 67328647, compound → HCID 67328728, compound

HRID 1846165Notes

Reaction equation

HRID 1846165 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10]([CH3:12])[CH3:11])[CH:4]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][O:25][CH3:26].[Li]CCCC>C1COCC1.CCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][O:25][CH3:26])[N:6]=[C:5]([N:10]([CH3:12])[CH3:11])[CH:4]=1

Participants

6

Reactant 3

HCID 67328647HCID 67328647, compoundHCID 85780880HCID 85780880, compoundHCID 178418339Butyllithium

Product 1

HCID 67328728HCID 67328728, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 156 mg (0.94 mmol) of 4-methoxy-N,N,6-trimethylpyridin-2-amine in 5 mL of anhydrous THF were added 252 mg (0.94 mmol) of 1-bromo-9-(methoxymethoxy)nonane followed by 650 μL (1.04 mmol) of 1.6M n-BuLi in pentane. The reaction mixture was stirred at 23° C. for 15 min. The reaction was quenched with satd. aq. ammonium chloride and poured into 50 mL of water. The mixture was extracted with two 50-mL portions of ethyl acetate. The combined organic solution was washed with a 50-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 1:1 hexanes-ethyl acetate afforded the expected product as yellowish oil: yield 235 mg (70%); silica gel TLC Rf 0.47 (1:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.24 (br m, 12H), 1.55 (quint, 2H, J=6.4 Hz), 1.68 (quint, 2H, J=7.6 Hz), 2.55 (dd, 2H, J=7.6, 7.6 Hz), 3.03 (s, 6H), 3.46 (s, 3H), 3.49 (t, 2H, J=6.8 Hz), 3.76 (s, 3H), 4.59 (s, 2H), 5.77 (s, 1H) and 6.01 (s, 1H); 13C NMR (CDCl3) δ 26.17, 29.25, 29.39, 29.48, 29.50, 29.55, 29.60, 29.62, 29.72, 37.96, 37.96, 54.63, 55.01, 67.85, 87.44, 96.36, 97.86, 160.77, 162.05 and 167.41; mass spectrum (APCI), m/z (M+H)+353.2808 (C20H37N2O3 requires 353.2804).

Workup

  1. customThe reaction was quenched with satd
  2. additionaq. ammonium chloride and poured into 50 mL of water
  3. extractionThe mixture was extracted with two 50-mL portions of ethyl acetate
  4. washThe combined organic solution was washed with a 50-mL portion of brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under diminished pressure
  7. customThe residue was purified by chromatography on a silica gel column (3×10 cm)
  8. washElution with 1:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-4f54f31d26f143ada177776a54b524f8
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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