Ethyl bromoacetate → 2-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-naphthyi)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

HRID 344034Notes

Reaction equation

HRID 344034 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:14]1)[CH2:7]2.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:38]([O:37][C:35]([CH2:34][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:14]1)[CH2:7]2)=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 701861852-[(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone

Product 1

HCID 701875372-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-naphthyi)methyl]-6-diphenylmethyl-3(2H)-pyridazinoneYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-[(1,2,3,4-tetrahydro-5-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (425 mg), ethyl bromoacetate (184 mg) and potassium carbonate (152.9 mg) in acetonitrile (15 ml) was refluxed for 6 hours. After cooling, the precipitated solid was filtered off and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 2-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-naphthyi)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.43 g) as pale yellow oil.

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0be8d084f10c4a1dbcf670d33dea57d2
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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