2-Acetylnaphthalene → HCID 86743478, compound

HRID 2352407Notes

Reaction equation

HRID 2352407 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:20]=[CH:19][C:9]([CH2:10]P(=O)(OCC)OCC)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[C:23]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)(=O)C.O1CCC[CH2:37]1>O1CCOCCOCCOCCOCC1.ClC(Cl)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([CH3:37])=[CH:23][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)=[CH:19][CH:20]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 71222-AcetylnaphthaleneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoate

Product 1

HCID 86743478HCID 86743478, compound

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

31 g of diethyl 4-ethoxycarbonyl-benzylphosphonate and a few drops of 1,4,7,10,13-pentaoxa-cyclopentadecane are added to a suspension of 5.5 g of sodium hydride in 100 cm3 of tetrahydrofuran. The mixture is stirred at 45° C. for one hour and 17 g of 2-acetyl-naphthalene are then added. It is kept at 45° C. for three hours, allowed to cool, then diluted with dichloroethane. The insoluble matter is filtered off and the filtrate is evaporated under reduced pressure. The residue is recrystallised twice from ethanol. 14 g of the expected product are obtained. Melting point: 96° C.

Workup

  1. waitIt is kept at 45° C. for three hours
  2. temperatureto cool
  3. filtrationThe insoluble matter is filtered off
  4. customthe filtrate is evaporated under reduced pressure
  5. customThe residue is recrystallised twice from ethanol

Sources & evidence

ORD record
ord-2c73df5cc4e740548b913a7f50703d39
Source dataset
uspto-grants-1989_10
Patent number
US04876381

Reaction notes

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