2,4-Pentadienoic acid, methyl ester → HCID 20435989, compound

HRID 1154034Notes

Reaction equation

HRID 1154034 reaction equation
[CH3:1][C:2]1([CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6](=[O:7])[NH:5][NH:4][C:3]1=[O:8].[C:18]([O:24][CH3:25])(=[O:23])[CH:19]=[CH:20][CH:21]=[CH2:22].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>ClCCl>[CH3:1][C:2]1([CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:6](=[O:7])[N:5]2[CH2:22][CH:21]=[CH:20][CH:19]([C:18]([O:24][CH3:25])=[O:23])[N:4]2[C:3]1=[O:8]

Participants

5

Reactant 3

HCID 736882,4-Pentadienoic acid, methyl esterHCID 20435928HCID 20435928, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 20435989HCID 20435989, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(B)(b) A mixture of 14.52 g (0.06 mol) of 4-methyl-4-[2-(tetrahydro-2-pyranyloxy)ethyl]pyrazolidine-3,5-dione and 6.72 g (0.066 mol) of methyl penta-2,4-dienoate in 150 ml of dry dichloromethane was stirred at room temperature under a stream of nitrogen. A solution of 26.64 g (0.06 mol) of lead tetraacetate in 100 ml of dry dichloromethane was added dropwise, the blue color being allowed to fade between additions. When the addition was complete and no blue color persisted, the resulting suspension was filtered. The filtrate was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to give 8.12 g (38%) of methyl 2,3,5,8-tetrahydro-2-methyl-1,3-dioxo-2-[2-(tetrahydro-2-pyranyloxy)ethyl]-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate having a melting point of 126.5°-127.6° C. (from diethyl ether).

Workup

  1. additionWhen the addition
  2. filtrationthe resulting suspension was filtered
  3. washThe filtrate was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ded641e9cef2437dbf76b1aa9e60a607
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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