Hydrochloric Acid → N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline

HRID 52489Notes

Reaction equation

HRID 52489 reaction equation
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]

Participants

6

Reactant 5

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

Product 1

HCID 67722040N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinolineYield 54%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0510ebea3cd24b92a81b989732cdd202
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…