Hydrochloric Acid → 5-Methyl-6-oxoheptanesulfonic acid

HRID 40427

反応式

HRID 40427 の反応式
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3](OCC)=O.[H-].[Na+].[CH2:13]1C[O:19][S:16](=[O:18])(=[O:17])[CH2:15][CH2:14]1.[OH-].[Na+].Cl>CN(C=O)C.O>[CH3:1][CH:2]([C:8](=[O:9])[CH3:10])[CH2:3][CH2:13][CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 14798Sodium HydroxideHCID 154111,4-Butane sultoneHCID 24758Sodium hydride

生成物 1

HCID 579033515-Methyl-6-oxoheptanesulfonic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

Ethyl 2-methylacetoacetate (50 g) in DMF (25 ml) was added to a suspension of sodium hydride (12.0 g of 60% NaH in mineral oil) in DMF (100 ml), dropwise with ice-bath cooling over 1 hour, (internal temperature 0-4° C.). This mixture was allowed to warm to ambient temperature for 45 mins with stirring before re-cooling. A solution of 1,4-butanesultone (45 g) in DMF (25 ml) was then added dropwise over 15 minutes. The final mixture was heated at 60° C. for 18 hours. The solvent was removed by rotary evaporation and the residue partitioned between water and diethyl ether. The aqueous layer was collected, washed with fresh diethyl ether and rotary evaporated to yield a sticky foam. This intermediate was dissolved in water (100 ml) and sodium hydroxide (17.8 g) added over 15 minutes with stirring. The mixture was heated at 90° C. for 18 hours. The cooled reaction mixture was adjusted to ˜pH2 by the addition of concentrated hydrochloric acid (˜40 ml). The solution was rotary evaporated and dried under vacuum. The yellow solid was washed with ethanol containing 2% hydrochloric acid (3×150 ml). The ethanolic solution was filtered, rotary evaporated and dried under vacuum to yield a yellow solid. Yield 70 g.

後処理

  1. temperaturecooling over 1 hour
  2. custom(internal temperature 0-4° C.)
  3. temperaturebefore re-cooling
  4. customThe solvent was removed by rotary evaporation
  5. customthe residue partitioned between water and diethyl ether
  6. customThe aqueous layer was collected
  7. washwashed with fresh diethyl ether
  8. customrotary evaporated
  9. customto yield a sticky foam
  10. stirringwith stirring
  11. temperatureThe mixture was heated at 90° C. for 18 hours
  12. customThe cooled reaction mixture
  13. customThe solution was rotary evaporated
  14. customdried under vacuum
  15. washThe yellow solid was washed with ethanol containing 2% hydrochloric acid (3×150 ml)
  16. filtrationThe ethanolic solution was filtered
  17. customrotary evaporated
  18. customdried under vacuum
  19. customto yield a yellow solid

出典と根拠

ORDレコード
ord-dc1b563f1b5047ec897e3bd65136287a
出典データセット
uspto-grants-2013_09
特許番号
US08529874B2

関連ノート

読み込み中…