1-Bromo-2-methylpropane → 2-Isobutyl-3-ketoglutarate diethyl ester

HRID 1031245

反応式

HRID 1031245 の反応式
[O:1]=[C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-]CC.[Mg+2].[O-]CC.Br[CH2:23][CH:24]([CH3:26])[CH3:25]>>[CH3:23][CH:24]([CH3:26])[CH2:25][CH:9]([C:2](=[O:1])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

4

反応物 3

HCID 65551-Bromo-2-methylpropane2 回HCID 66045Diethyl acetonedicarboxylateHCID 164963Magnesium ethanolate

生成物 1

HCID 99926592-Isobutyl-3-ketoglutarate diethyl ester収率 62%

実験手順

Diethyl 3-oxopentanedioate (45.5 ml, 0.25 mol) was added to a suspension of magnesium ethoxide (prepared from magnesium turnings (9 g, 0.375 mol) and iodine (0.1 g) in dry ethanol (275 ml)), and the mixture was heated under reflux for 90 min. 1-Bromo-2-methylpropane (54 ml, 0.5 mol) was added, and the reaction was heated under reflux for 16 h. Further 1-bromo-2-methylpropane (27 ml, 0.25 mol) was added to the boiling mixture, and after 3 h the solvent was evaporated in vacuo. The residue was partitioned between 2 N hydrochloric acid and ether. After extracting the aqueous phase with ether, the combined organics were washed successively with water, 5% sodium bicarbonate, water and brine, then were dried (Na2SO4) and evaporated in vacuo. The residue was distilled to give the title compound as a colourless oil (40 g, 62%), bp 118°-120° C. (1 mmHg). δ (CDCl3): 0.9 (6H, d, J=6Hz), 1.25 (6H, t, J=7Hz), 1.4-1.9 (3H, m), 3.5 (2H, s), 3.7 (1H, d, J=9Hz) and 4.2 (4H, q, J=7Hz).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 90 min
  3. temperaturethe reaction was heated
  4. temperatureunder reflux for 16 h
  5. customafter 3 h the solvent was evaporated in vacuo
  6. customThe residue was partitioned between 2 N hydrochloric acid and ether
  7. extractionAfter extracting the aqueous phase with ether
  8. washthe combined organics were washed successively with water, 5% sodium bicarbonate, water and brine
  9. dry with materialwere dried (Na2SO4)
  10. customevaporated in vacuo
  11. distillationThe residue was distilled

出典と根拠

ORDレコード
ord-9f409073cecb4cee984edb22c535e47b
出典データセット
uspto-grants-1992_04
特許番号
US05109000

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