m-Chloroperbenzoic acid → HCID 70186183, compound

HRID 344065Notes

Reaction equation

HRID 344065 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12]([CH2:18][N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20]1)=[CH:13]2)=[O:5])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:44]>ClCCl>[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12]([CH2:18][N:19]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:20]1)([OH:44])[CH2:13]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70186194HCID 70186194, compound

Product 1

HCID 70186183HCID 70186183, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(3,4-dihydro-5-ethoxycarbonylmethoxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.20 g) and 3-chloroperoxybenzoic acid (94 mg) in dichloromethane (5 ml) was allowed to stand in a freezer (about -15° C.) for overnight. The reaction mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and sodium hydrogencarbonate solution. The organic layer was separated and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo. The residue and 10% palladium on carbon in ethyl acetate (5 ml) and acetic acid (one drop) were stirred under hydrogen (1 atm) at room temperature for 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate=2:1~1:1) to give 2-[(1,2,3,4-tetrahydro-5-ethoxycarbonylmethoxy-2-hydroxy-2-naphthyl)methyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.08 g) as a pale yellow oil.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and sodium hydrogencarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. filtrationThe catalyst was filtered off
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate=2:1~1:1)

Sources & evidence

ORD record
ord-73ade45838a94c77b3d77b2414ae1b6d
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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