Dimethyl 3-oxoglutarate → HCID 178500932, compound

HRID 386551Notes

Reaction equation

HRID 386551 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])(=O)C.[Na+].[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([N+:28]#[N:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>C(O)C.O>[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([NH:28]/[N:29]=[C:8](\[C:2](=[O:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])/[C:9]([O:11][CH3:12])=[O:10])=[CH:26][CH:27]=1)(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 74591Dimethyl 3-oxoglutarateHCID 517045Sodium AcetateHCID 86658657HCID 86658657, compound

Product 1

HCID 178500932HCID 178500932, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of dimethyl 3-oxopentanedioate (3.48 g, 20 mmol) in ethanol (12 mL) and water (40 mL) at room temperature was added sodium acetate (12.0 g, 146 mmol), and was followed by addition of 4-(methylsulfonyl)benzenediazonium solution (20 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The product was collected by filtration, then washed with water (˜50 mL) and dried overnight under reduce pressure to yield 7.0 g (83%) of (E)-dimethyl 2-(2-(4-(methylsulfonyl)phenyl)hydrazono)-3-oxopentanedioate as a yellow solid. MS (ESI) 357 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe product was collected by filtration
  3. washwashed with water (˜50 mL)
  4. customdried overnight

Sources & evidence

ORD record
ord-db1a2854455949b49cbba6bacbeb98fe
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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