Ethyl 2-methylacetoacetate → Diethyl 2-acetyl-2-methyloctanedioate

HRID 579407ノート

反応式

HRID 579407 の反応式
[CH3:1]C(C)([O-])C.[K+].CC(C)([O-])C.[CH3:12][CH:13]([C:19]([CH3:21])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH2:22]([O:24][C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29]CBr)[CH3:23]>C(O)(C)(C)C>[C:19]([C:13]([CH3:1])([CH2:12][CH2:29][CH2:28][CH2:27][CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:32])[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:20])[CH3:21]

参加物

6

反応物 4

HCID 701Ethyl 2-methylacetoacetateHCID 117544Ethyl 6-bromohexanoateHCID 45749132-Methylpropan-2-olateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 22266834Diethyl 2-acetyl-2-methyloctanedioate収率 72,751.203%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50° C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.

後処理

  1. dissolutiontotally dissolved
  2. stirringthe reaction mixture was stirred
  3. temperaturerefluxed for 5 hours
  4. filtrationThe mixture was filtered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was partitioned between 1M HCl and chloroform
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. custompurified on silica gel using 1:10 ethyl acetate/hexane as the eluent

出典と根拠

ORDレコード
ord-db0bca3c94274489840839d5a6b08767
出典データセット
uspto-grants-2015_05
特許番号
US09040721B2

反応ノート

読み込み中…