Pentane → Ethyl p-[2-(1,2,3,4-tetrahydro-1,4,4-trimethyl-7-quinolinyl)propenyl]benzoate

HRID 37405Notes

Reaction equation

HRID 37405 reaction equation
[H-].[Na+].CCCCC.[C:8]([C:13]1[CH:27]=[CH:26][C:16]([CH2:17]P(=O)(OCC)OCC)=[CH:15][CH:14]=1)([O:10][CH2:11][CH3:12])=[O:9].[CH3:28][C:29]([C:31]1[CH:40]=[C:39]2[C:34]([C:35]([CH3:43])([CH3:42])[CH2:36][CH2:37][N:38]2[CH3:41])=[CH:33][CH:32]=1)=O>CN(C)C=O>[CH3:41][N:38]1[C:39]2[C:34](=[CH:33][CH:32]=[C:31]([C:29]([CH3:28])=[CH:17][C:16]3[CH:15]=[CH:14][C:13]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:27][CH:26]=3)[CH:40]=2)[C:35]([CH3:42])([CH3:43])[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 199353911,2,3,4-Tetrahydro-1,4,4-trimethyl-7-quinolinyl methyl ketone

Product 1

HCID 53694147Ethyl p-[2-(1,2,3,4-tetrahydro-1,4,4-trimethyl-7-quinolinyl)propenyl]benzoateYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

2.9 g of a 50% suspension of sodium hydride in mineral oil were suspended in 30 ml of dimethylformamide after two-fold Washing with pentane and treated dropwise at room temperature with a solution of 17.3 g of diethyl (4-carbethoxybenzyl)phosphonate in 50 ml of dimethylformamide. After stirring at room temperature for 1 hour, a solution of 5 g of 1,2,3,4-tetrahydro-1,4,4-trimethyl-7-quinolinyl methyl ketone in 50 ml of dimethylformamide was added dropwise thereto. The reaction mixture was heated to 50° C. for 1 hour, poured on to ice/water and extracted with ethyl acetate. The brownish oil obtained after drying and evaporation of the organic phase was chromatographed (silica gel, eluting agent hexane/ethyl acetate=9:1) and gave 4.2 g of ethyl p-[2-(1,2,3,4-tetrahydro-1,4,4-trimethyl-7-quinolinyl)propenyl]benzoate as a slightly yellow, viscous oil.

Workup

  1. temperatureThe reaction mixture was heated to 50° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. customThe brownish oil obtained
  4. customafter drying
  5. customevaporation of the organic phase
  6. customwas chromatographed
  7. wash(silica gel, eluting agent hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e7660061cebf43aba66914fd4900744e
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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