Sodium hydride → HCID 54242798, compound

HRID 232861Notes

Reaction equation

HRID 232861 reaction equation
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.O=[C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][O:18][C:17]2[CH:26]=[CH:27][C:28]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:29][C:16]1=2.[H-].[Na+]>C(COC)OC>[CH3:13][O:12][C:10]([CH:9]=[C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][O:18][C:17]2[CH:26]=[CH:27][C:28]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:29][C:16]1=2)=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 23359165HCID 23359165, compound

Product 1

HCID 54242798HCID 54242798, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

1.1 ml of methyl diethylphosphonoacetate dissolved in 10 ml of dimethoxyethane was added to 1.84 g of 11-oxo-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine and 0.3 g of 64% by weight sodium hydride suspended in 20 ml of dimethoxyethane and the mixture was refluxed under heating for 5 hours. The solvent was removed from the reaction mixture, the residue was dissolved in ethyl acetate and the organic layer was washed with water and a saturated saline solution and then dried over anhydrous sodium sulfate. After the solvent was removed from the solution, the residue was applied to silica gel column chromatography to obtain 2.3 g of 11-methoxycarbonylmethylene-2-(quinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine as a brown oily product.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. customThe solvent was removed from the reaction mixture
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
  7. customAfter the solvent was removed from the solution

Sources & evidence

ORD record
ord-839f965ad9c240c69ed2654a14d7b3a2
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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