Water → (E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidine

HRID 488147Notes

Reaction equation

HRID 488147 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])(OCC)=O)C.[CH2:20]([C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[C:24]([O:36]COC)=[C:25]([O:34][CH3:35])[CH:26]=[C:27]2[CH:32]=O)[CH3:21].O>CN(C)C=O>[CH2:20]([C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[C:24]([OH:36])=[C:25]([O:34][CH3:35])[CH:26]=[C:27]2/[CH:32]=[CH:11]/[C:12]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:13])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 99705695-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehydeHCID 13203262Diethyl [2-oxo-2-(piperidin-1-yl)ethyl]phosphonate

Product 1

HCID 14986482(E)-1-[3-(5-ethyl-4-hydroxy-3-methoxy-1-naphthyl)-1-oxo-2-propenyl]piperidineYield 111.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.15 g of 60% sodium hydride was suspended in 20 ml of N,N-dimethylformamide, to which 1.15 g of N-(diethoxyphosphoryl)acetylpiperidine was gradually added at room temperature. After stirring for 10 minutes, a solution of 800 mg of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde in N,N-dimethylformamide (10 ml) was gradually added. After stirring for 20 minutes, water was added, followed by extraction with ethyl acetate. The combined extracts were washed with water and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain 1.1 g of the titled compound as pale yellow crystals.

Workup

  1. additionwas gradually added at room temperature
  2. stirringAfter stirring for 20 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent
  7. customthe resultant residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e41e6052f6274f1a9ff49ba561439c8f
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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