Disodium 2-oxoglutarate → HCID 131731097, compound

HRID 1914469Notes

Reaction equation

HRID 1914469 reaction equation
[Na+].[Na+].[O:3]=[C:4]([CH2:8][CH2:9][C:10]([O-:12])=[O:11])[C:5]([O-:7])=[O:6].[Br-].[C:14]1([S+:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.ClCCl>[O:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:5]([OH:7])=[O:6].[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 31040Disodium 2-oxoglutarateHCID 11984010Triphenylsulfonium Bromide2×

Product 1

HCID 131731097HCID 131731097, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-ketoglutaric acid disodium salt (0.4 g, 2.1 mmol) was dissolved in 6 mL of water. Triphenylsulfonium bromide (1.4 g, 4.1 mmol) was dissolved in 12 mL dichloromethane. The salt solution was added dropwise to the triphenylsulfonium bromide solution and the mixture was stirred overnight at room temperature. The reaction mixture was evaporated to dryness (or on oil stage) on a rotary evaporator. The product obtained from evaporation was washed with ethyl ether and dissolved using an excess amount of dichloromethane and filtered. After the evaporation of dichloromethane, the pure compound was obtained as a white solid.

Workup

  1. customThe reaction mixture was evaporated to dryness (or on oil stage) on a rotary evaporator
  2. customThe product obtained from evaporation
  3. washwas washed with ethyl ether
  4. dissolutiondissolved
  5. filtrationfiltered
  6. customAfter the evaporation of dichloromethane
  7. customthe pure compound was obtained as a white solid

Sources & evidence

ORD record
ord-71beb9f1111e49e89696b92c87c01c4b
Source dataset
uspto-grants-2013_12
Patent number
US08614047B2

Reaction notes

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