Methylglyoxal → 2,5-Dioxo-3-hydroxy-8-nonyne

HRID 66951

反応式

HRID 66951 の反応式
[OH-:1].[Na+].S(=O)(=O)(O)O.[CH3:8][C:9]([CH:11]=[O:12])=[O:10].[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:10]=[C:9]([CH:11]([OH:12])[CH2:13][C:14](=[O:1])[CH2:15][CH2:16][C:17]#[CH:18])[CH3:8]

参加物

5

反応物 4

HCID 880MethylglyoxalHCID 1118Sulfuric AcidHCID 1140TolueneHCID 14798Sodium Hydroxide

生成物 1

HCID 129396472,5-Dioxo-3-hydroxy-8-nonyne収率 82%

反応条件

温度
30 °C

実験手順

To dimethyl 2-(2'-propynyl)-3-oxoglutarate (21.2 g) was added a 10% aqueous sodium hydroxide solution (sodium hydroxide 8.0 g, water 72 ml) with ice cooling, followed by stirring at 30° C. for 5 hours. The pH of the reaction solution was adjusted to 7.5 with a 10% sulfuric acid with ice cooling, and toluene (60 ml) was added thereto. While passing nitrogen stream, a 40.7% aqueous methylglyoxal solution (20 g) was added dropwise to the reaction solution at 35° C. over 2 hours. Thereafter, the reaction solution was stirred at 35° C. for 15 hours. The reaction solution was separated into two layers, and the aqueous layer was saturated with sodium chloride and extracted four times with ethyl acetate. The toluene layer and the ethyl acetate layer were combined, and the solvent was removed by evaporation to obtain 13.8 g of 2,5-dioxo-3-hydroxy-8-nonyne as a pale yellow oil (yield 82.0%).

後処理

  1. additionwas added
  2. stirringThereafter, the reaction solution was stirred at 35° C. for 15 hours
  3. customThe reaction solution was separated into two layers
  4. extractionextracted four times with ethyl acetate
  5. customthe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-b887613c0bbc4e759a91451080bfc5ef
出典データセット
uspto-grants-1982_08
特許番号
US04343953

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