Water → Ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenoate

HRID 378379Notes

Reaction equation

HRID 378379 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][CH:18]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30](=O)[CH3:31])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:21]1)[CH3:19].O>CN(C)C=O>[CH3:19][CH:18]([N:20]1[C:29]2[C:24](=[CH:25][C:26](/[C:30](/[CH3:31])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:21]1)[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 107751501-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone

Product 1

HCID 10517412Ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenoateYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (60%, 51 mmol) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide, and 11.3 g (51 mmol) of ethyl diethylphosphonoacetate was dropped into the suspension under cooling with ice. The obtained mixture was stirred at room temperature for one hour, followed by the addition of 5.5 g (25 mmol) of 1-[1-(1-methylethyl)-1,2,3,4-tetra-hydroquinolin-6-yl]ethanone. The obtained mixture was stirred at 60° C. for 48 hours, followed by the addition of water. The mixture thus obtained was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography (4% ethyl acetate/n-hexane) to give 4.0 g of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred at 60° C. for 48 hours
  3. customThe mixture thus obtained
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with a saturated aqueous solution of common salt
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in a vacuum
  8. customThe residue was purified by silica gel column chromatography (4% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-a5701764f03a45c890c5bb630c05222e
Source dataset
uspto-grants-2000_02
Patent number
US06030964

Reaction notes

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