Hydrochloric Acid → N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline

HRID 52489노트

반응식

HRID 52489 반응식
C[C:2]([CH3:5])([O-:4])C.[K+].[C:7]([N:14]1[C:23]2[CH:18]([CH2:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[CH:24]=O)([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8].O.Cl.C1C[O:31][CH2:30][CH2:29]1>>[C:7]([N:14]1[C:23]2[CH:18]([CH2:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[CH:24]=[CH:29][C:30]([O:4][CH2:2][CH3:5])=[O:31])([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2회HCID 23665647Potassium tert-butoxideHCID 86750625N-ethoxalyl-2-formyltetrahydroquinoline

생성물 1

HCID 67722040N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline수율 54%

실험 절차

To a solution of diethylphosphonoacetic acid diethyl ester (10.6 g, 47.1 mmol) in THF (100 mL) was added potassium tert-butoxide (5.04 g, 44.9 mmol) at 0° C. The mixture was stirred for 20 min at room temperature. To the solution was added dropwise N-ethoxalyl-2-formyltetrahydroquinoline (11.18 g, 42.8 mmol)in THF (120 mL) at 0° C. After the complete addition, the mixture was stirred for 15 min at room temperature and water and a small amount of diluted hydrochloric acid were added. The mixture was extracted with ethyl acetate. The organic layer was washed three times with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 3:1 hexane/ethyl acetate to give 7.63 g of N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline (54%): 1H NMR (270 MHz, CDCl3) δ7.15 (m, 4H), 6.79 (dd, 1H, J=16, 5 Hz), 5.89 (dd, 1H, J=16, 2 Hz), 5.31 (m, 1H), 4.12 (q, 2H, J=7 Hz), 2.73 (t, 2H, J=6 Hz), 2.47 (m, 1H), 1.69 (m, 1H), 1.25 (t, 3H, J=7 Hz), 1.11 (t, 3H, J=7 Hz).

후처리

  1. additionAfter the complete addition
  2. stirringthe mixture was stirred for 15 min at room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed three times with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 4:1 to 3:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-0510ebea3cd24b92a81b989732cdd202
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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