Ethyl 2-methylacetoacetate → 5-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid

HRID 1667359

反応式

HRID 1667359 の反応式
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:13]1[CH2:20][O:19][S:16](=[O:18])(=[O:17])[CH2:15][CH2:14]1>CN(C)C=O>[CH2:6]([O:5][C:3]([C:2]([CH3:1])([C:8](=[O:9])[CH3:10])[CH2:20][CH2:13][CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17])=[O:4])[CH3:7]

参加物

5

反応物 3

HCID 701Ethyl 2-methylacetoacetateHCID 154111,4-Butane sultoneHCID 24758Sodium hydride

生成物 1

HCID 580840065-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid収率 122.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

Ethyl 2-methylacetoacetate (43.2 g) in N,N-dimethylformamide (25 ml) was added to a suspension of sodium hydride (12.0 g of 60% NaH in mineral oil) in N,N-dimethylformamide (100 ml), dropwise with ice-bath cooling. This mixture was allowed to warm to ambient temperature for 30 mins before re-cooling. 1,4-butanesultone (40.8 g) in N,N-dimethylformamide (25 ml) was then added dropwise. The final mixture was heated at 50° C. for 18 hrs, then quenched with 50 ml of water. The solvent was evaporated under vacuum; the residue was partitioned between water and diethyl ether. The aqueous layer was collected, washed with fresh diethyl ether and evaporated under vacuum; final drying was under high vacuum over phosphorus pentoxide. A yield of 103 g of 5-(ethoxycarbonyl)-5-methyl-6-oxoheptane-1-sulfonic acid was obtained.

後処理

  1. temperaturecooling
  2. temperaturebefore re-cooling
  3. customquenched with 50 ml of water
  4. customThe solvent was evaporated under vacuum
  5. customthe residue was partitioned between water and diethyl ether
  6. customThe aqueous layer was collected
  7. washwashed with fresh diethyl ether
  8. customevaporated under vacuum
  9. customfinal drying

出典と根拠

ORDレコード
ord-a84c320341604e82bcceda72e086f20b
出典データセット
uspto-grants-2011_10
特許番号
US08044203B2

関連ノート

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