Hydrochloric Acid → N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline

HRID 52489ノート

反応式

HRID 52489 の反応式
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]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 23665647Potassium tert-butoxideHCID 86750625N-ethoxalyl-2-formyltetrahydroquinoline

生成物 1

HCID 67722040N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline収率 54%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0510ebea3cd24b92a81b989732cdd202
出典データセット
uspto-grants-1997_04
特許番号
US05616586

反応ノート

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