HCID 67328647, 화합물 → HCID 67328728, 화합물

HRID 1846165노트

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HRID 1846165 반응식
[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

참가 물질

6

반응물 3

HCID 67328647HCID 67328647, 화합물HCID 85780880HCID 85780880, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67328728HCID 67328728, 화합물

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

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온도
23 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4f54f31d26f143ada177776a54b524f8
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952025B2

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