Ethyl bromoacetate → HCID 19082461, compound

HRID 963728Notes

Reaction equation

HRID 963728 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[CH2:12][CH2:13][N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:15]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>CN(C)C=O>[CH2:45]([O:44][C:42]([CH2:41][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[CH2:12][CH2:13][N:14]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:15]1)=[O:43])[CH3:46]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 70187529HCID 70187529, compound

Product 1

HCID 19082461HCID 19082461, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A N,N-dimethylformamide solution (15 ml) of crude 2-[2-(5-hydroxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.34 g), potassium carbonate (0.16 g) and ethyl bromoacetate (0.2 ml) was stirred at room temperature for 24 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane-ethyl acetate=3:2) over silica gel to afford 2-[2-(5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]-6-diphenylmethyl-3(2H)-pyridazinone (0.17 g) as a pale yellow oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (n-hexane-ethyl acetate=3:2) over silica gel

Sources & evidence

ORD record
ord-e4efda210324459f8d8bc6d9957675bf
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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